Pyrimidin-4-one derivatives, their intermediates for their production and processes for producing these compounds

ABSTRACT

Novel pyrimidin-4-one derivatives of formula [1] are provided, which are useful as active ingredients of herbicides, wherein R 1  is hydrogen or alkyl; R 2  is alkyl optionally substituted with halogen; R 3  is alkyl optionally substituted with halogen, alkenyl, or alkynyl; and Q is substituted phenyl. Also provided are intermediates for their production and processes for producing these intermediates.

This application is the national phase under 35 U.S.C. §371 of prior PCTInternational Application No. PCT/JP 96/02169 which has an Internationalfiling date of Aug. 1, 1996 which designated the United States ofAmerica, the entire contents of which are hereby incorporated byreference.

TECHNICAL FIELD

The present invention relates to pyrimidin-4-one derivatives, their use,intermediates for their production, and processes for producing theseintermediates.

BACKGROUND ART

GB-A-2 130 214 discloses some pyrimidin-4-one derivatives havingherbicidal activity.

DE-A-38 16 994 discloses some 2-haloalkyl-4-hydroxy pyrimidinederivatives.

Chemical Abstracts 51:9629g (1957) discloses6-ethyl-5-(4-chlorophenyl)-2-dichloromethyl-3H-pyrimidin-4-one.

Chemical Abstracts 88:152546n (1978) discloses some2-methyl-pyrimidin-4-one derivatives.

EP-A-0 168 262 discloses that some 2-alkyl-pyrimidin-4-one derivativesare useful in the treatment of heart diseases, hypertension,cerebrovascular diseases and thrombosis.

EP-A-0 544 166 discloses some 2-methyl4(3H)-pyrimidone compounds.

EP-A-0 568 041 discloses that some3-phenyl-6-trifluoromethylpyrimidin-4-one derivatives have herbicidalactivity.

EP-A-0 561 319 discloses that some pyrimidin-2,6-dione compounds haveherbicidal activity.

EP-A-0 617 033 discloses that some pyrimidin-2,5-dione compounds haveherbicidal activity.

DISCLOSURE OF INVENTION

The present inventors have intensively studied to find a compound havingexcellent herbicidal activity. As a result, they have found thatpyrimidin-4-one derivatives represented by formula [1] as depicted belowhave excellent herbicidal activity, thereby completing the presentinvention.

Thus the present invention provides a compound of the formula: ##STR1##wherein R¹ is hydrogen or C₁ -C₃ alkyl; R² is C₁ -C₃ alkyl optionallysubstituted with one or more halogen atoms; R³ is C₁ -C₆ alkyloptionally substituted with one or more halogen atoms, C₃ -C₆ alkenyl,or C₃ -C₆ alkynyl; and Q is substituted phenyl (hereinafter referred toas the present compound(s)); and a herbicide containing it as an activeingredient.

The present invention also provides a process for producing compound[1], which comprises reacting a compound of the formula: ##STR2##wherein Q, R¹, and R² are as defined above, with a compound of theformula:

    R.sup.3 --D                                                [3]

wherein D is chlorine, bromine, iodine, methanesulfonyloxy,trifluoromethanesulfonyloxy, or p-toluenesulfonyloxy; and R³ is asdefined above.

The present invention further provides a compound of the formula:##STR3## wherein Q and R¹ are as defined above; R²¹ is C₁ -C₃ alkylsubstituted with one or more halogen atoms, which is useful as anintermediate for the production of some of the present compounds; and aprocess for producing a compound of the formula: ##STR4## wherein Q, R¹, and R² are as defined above, which comprises reacting a compound ofthe formula: ##STR5## wherein R¹⁹ and R²⁰ are independently C₁ -C₃alkyl, and Q and R¹ are as defined above, with a compound of theformula: ##STR6## wherein R² is as defined above.

The compound [2] may be present as a compound of the formula: ##STR7##which is a tautomer thereof.

Examples of Q in the present invention include [Q-1], [Q-2], [Q-3],[Q-4], or [Q-5] of the formula: ##STR8## wherein X is hydrogen orhalogen;

Y is halogen, nitro, cyano, or trifluoromethyl;

Z¹ is oxygen, sulfur, NH, or methylene;

Z² is oxygen or sulfur;

n is 0 or 1;

B is hydrogen, halogen, nitro, cyano, chlorosulfo, --OR¹⁰, --SR¹⁰, --SO₂--OR¹⁰, --N(R¹⁰)R¹¹, --SO₂ N(R¹¹)R¹², --NR¹¹ (COR¹³), --NR¹¹ (SO₂ R¹⁴),--N(SO₂ R¹⁴)--(SO₂ R¹⁵), --N(SO₂ R¹⁴)(COR¹³), --NHCOOR¹³, --COOR¹³,--CON(R¹¹)R¹², --CSN--(R¹¹)R¹², --COR¹⁶, --CR¹⁷ ═CR¹⁸ CHO, --CR¹⁷ ═CR¹⁸COOR¹³, CR¹⁷ ═CR¹⁸ CON--(R¹¹)R¹², --CH₂ CHWCOOR¹³, or --CH₂CHWCON(R¹¹)R¹², wherein W is hydrogen, chlorine, or bromine; R¹⁰ ishydrogen, C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₃ -C₈ cycloalkyl, C₃ -C₆alkenyl, C₃ -C₆ haloalkenyl, C₃ -C₆ alkynyl, C₃ -C₆ haloalkynyl, cyanoC₁ -C₆ alkyl, C₂ -C₈ alkoxyalkyl, C₂ -C₈ alkylthioalkyl, carboxy C₁ -C₆alkyl, (C₁ -C₆ alkoxy)carbonyl C₁ -C₆ alkyl, (C₁ -C₆ haloalkoxy)carbonylC₁ -C₆ alkyl, {(C₁ -C₄ alkoxy) C₁ -C₄ alkoxy}carbonyl C₁ -C₆ alkyl, (C₃-C₈ cycloalkoxy)carbonyl C₁ -C₆ alkyl, --CH₂ CON(R¹¹)R¹², --CH₂COON(R¹¹)R¹², --CH(C₁ -C₄ alkyl)CON(R¹¹)R¹², or --CH(C₁ -C₄alkyl)COON(R¹¹)R¹² ; R¹¹ and R¹² are independently hydrogen, C₁ -C₆alkyl, C₁ -C₆ haloalkyl, C₃ -C₆ alkenyl, C₃ -C₆ alkynyl, cyano C₁ -C₆alkyl, C₂ -C₈ alkoxyalkyl, C₂ -C₈ alkylthioalkyl, carboxy C₁ -C₆ alkyl,(C₁ -C₆ alkoxy)carbonyl C₁ -C₆ alkyl, or {(C₁ -C₄ alkoxy) C₁ -C₄alkoxy}carbonyl C₁ -C₆ alkyl, or R¹¹ and R¹² are taken together to formtetramethylene, pentamethylene, or ethyleneoxyethylene; R¹³ is hydrogen,C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, or C₃ -C₈ cycloalkyl; R¹⁴ and R¹⁵ areindependently C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, or phenyl optionallysubstituted with methyl or nitro; R¹⁶ is hydrogen, C₁ -C₆ alkyl, C₁ -C₆haloalkyl, C₂ -C₆ alkenyl, C₂ -C₆ haloalkenyl, C₂ -C₆ alkynyl, C₂ -C₆haloalkynyl, C₂ -C₈ alkoxyalkyl, or hydroxy C₁ -C₆ alkyl; and R¹⁷ andR¹⁸ are independently hydrogen or C₁ -C₆ alkyl;

R⁴ is hydrogen or C₁ -C₃ alkyl,

R⁵ is hydrogen, C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₃ -C₆ alkenyl, C₃ -C₆haloalkenyl, C₃ -C₆ alkynyl, C₃ -C₆ haloalkynyl, cyano C₁ -C₆ alkyl, C₂-C₈ alkoxyalkyl, C₃ -C₈ alkoxyalkoxyalkyl, carboxy C₁ -C₆ alkyl, (C₁ -C₆alkoxy)carbonyl C₁ -C₆ alkyl, {(C₁ --C₄ alkoxy) C₁ -C₄ alkoxy}carbonylC₁ -C₆ alkyl, (C₃ -C₈ cycloalkoxy)carbonyl-C₁ -C₆ alkyl, --CH₂CON(R¹¹)R¹², --CH₂ COON(R¹¹)R¹², --CH(C₁ -C₄ alkyl)CON(R¹¹)R¹², --CH(C₁-C₄ alkyl)COON(R¹¹)R¹², C₂ -C₈ alkylthioalkyl, C₁ -C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, (C₁ --C₈ alkyl)carbonyl, (C₁ --C₈alkoxy)carbonyl, or hydroxy C₁ -C₆ alkyl;

R⁶ is C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, formyl, cyano, carboxyl, hydroxyC₁ -C₆ alkyl, C₁ -C₆ alkoxy C₁ -C₆ alkyl, C₁ -C₆ alkoxy C₁ -C₆ alkoxy C₁-C₆ alkyl, (C₁ -C₆ alkyl)carbonyloxy C₁ -C₆ alkyl, (C₁ -C₆haloalkyl)carbonyloxy C₁ -C₆ alkyl, (C₁ -C₆ alkoxy)carbonyl, or (C₁ -C₆alkyl)carbonyl;

R⁷ is hydrogen or C₁ -C₆ alkyl; and

R⁸ is C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₁ -C₆ hydroxyalkyl, C₂ -C₈alkoxyalkyl, C₃ -C₁₀ alkoxyalkoxyalkyl, (C₁ -C₅ alkyl)carbonyloxy C₁ -C₆alkyl, (C₁ -C₆ haloalkyl)carbonyloxy C₁ -C₆ alkyl, carboxyl, carboxy C₁-C₆ alkyl, (C₁ --C₈ alkoxy)carbonyl, (C₁ -C₆ haloalkoxy)carbonyl, (C₃-C₁₀ cycloalkoxy)carbonyl, (C₃ -C₈ alkenyloxy)carbonyl, (C₃ -C₈alkynyloxy)carbonyl, aminocarbonyl, (C₁ -C₆ alkyl)aminocarbonyl, di(C₁-C₆ alkyl)aminocarbonyl, (C₁ -C₆ alkyl)aminocarbonyloxy C₁ -C₆ alkyl, ordi(C₁ -C₆ alkyl)aminocarbonyloxy C₁ -C₆ alkyl.

In the above definition of the present compounds, the respectivesubstituents are exemplified as follows:

Examples of the C₁ -C₃ alkyl represented by R¹ include methyl, ethyl,and isopropyl.

Examples of the C₁ -C₃ alkyl optionally substituted with one or morehalogen atoms, which is represented by R², include methyl, ethyl,isopropyl, trichloromethyl, trifluoromethyl, difluoromethyl,chlorodifluoromethyl, and pentafluoroethyl.

Examples of the C₁ -C₆ alkyl optionally substituted with one or morehalogen atoms, which is represented by R³, include methyl, ethyl,isopropyl, difluoromethyl, and bromodifluoromethyl.

Examples of the C₃ -C₆ alkenyl represented by R³ include allyl and1-methyl-2-propenyl.

Examples of the C₃ -C₆ alkynyl represented by R³ include propargyl and1-methyl-2-propynyl.

In the formulas [Q-1], [Q-2], [Q-3], [Q-4], and [Q-5], the respectivesubstituents are exemplified as follows:

Examples of the halogen represented by X, Y, and B include chlorine,fluorine, bromine, and iodine.

Examples of the C₁ -C₆ alkyl represented by R¹⁰ include methyl, ethyl,isopropyl, propyl, isobutyl, butyl, t-butyl, amyl, isoamyl, and t-amyl.

Examples of the C₁ -C₆ haloalkyl represented by R¹⁰ includedifluoromethyl, tetrafluoroethyl, and 2,2,2-trifluoroethyl.

Examples of the C₃ -C₈ cycloalkyl represented by R¹⁰ includecyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

Examples of the C₃ -C₆ alkenyl represented by R¹⁰ include allyl,1-methyl-2-propenyl, 3-butenyl, 2-butenyl, 3-methyl-2-butenyl, and2-methyl-3-butenyl.

Examples of the C₃ -C₆ haloalkenyl represented by R¹⁰ include2-chloro-2-propenyl and 3,3-dichloro-2-propenyl.

Examples of the C₃ -C₆ alkynyl represented by R¹⁰ include propargyl,1-methyl-2-propynyl, 2-butynyl, and 1,1-dimethyl-2-propynyl.

Examples of the C₃ -C₆ haloalkynyl represented by R¹⁰ include3-bromo-2-propynyl.

Examples of the cyano C₁ -C₆ alkyl represented by R¹⁰ includecyanomethyl.

Examples of the C₂ -C₈ alkoxyalkyl represented by R¹⁰ includemethoxymethyl, methoxyethyl, ethoxymethyl, and ethoxyethyl.

Examples of the C₂ -C₈ alkylthioalkyl represented by R¹⁰ includemethylthiomethyl.

Examples of the carboxy C₁ -C₆ alkyl represented by R¹⁰ includecarboxymethyl, 1-carboxyethyl, and 2-carboxyethyl.

Examples of the (C₁ -C₆ alkoxy)carbonyl C₁ -C₆ alkyl represented by R¹⁰include methoxycarbonylmethyl, ethoxycarbonylmethyl,propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl,isobutoxycarbonylmethyl, t-butoxycarbonylmethyl, amyloxycarbonylmethyl,isoamyloxycarbonylmethyl, t-amyloxycarbonylmethyl,1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-propoxycarbonylethyl,1-isopropoxycarbonylethyl, 1-butoxycarbonylethyl,1-isobutoxycarbonylethyl, 1-t-butoxycarbonylethyl,1-amyloxycarbonylethyl, 1-isoamyloxycarbonylethyl, and1-t-amyloxycarbonylethyl.

Examples of the (C₁ -C₆ haloalkoxy)carbonyl C₁ -C₆ alkyl represented byR¹⁰ include 2,2,2-trifluoroethoxycarbonylmethyl.

Examples of the {(C₁ -C₄ alkoxy)C₁ -C₄ alkoxy}carbonyl C₁ -C₆ alkylrepresented by R¹⁰ include methoxymethoxycarbonylmethyl and1-methoxymethoxycarbonylethyl.

Examples of the (C₃ -C₈ cycloalkoxy)carbonyl C₁ -C₆ alkyl represented byR¹⁰ include cyclobutyloxycarbonylmethyl, cyclopentyloxycarbonylmethyl,cyclohexyloxycarbonylmethyl, 1-cyclobutyloxycarbonylethyl,1-cyclopentyloxycarbonylethyl, and 1 -cyclohexyloxycarbonylethyl.

Examples of the C₁ -C₆ alkyl represented by R¹¹ and R¹² include methyl,ethyl, propyl, butyl, isopropyl, and isobutyl.

Examples of the C₁ -C₆ haloalkyl represented by R¹¹ and R¹² includechloroethyl and bromoethyl.

Examples of the C₃ -C₆ alkenyl represented by R¹¹ and R¹² include allyl,1-methyl-2-propenyl, and 3-butenyl.

Examples of the C₃ -C₆ alkynyl represented by R¹¹ and R¹² includepropargyl and 1-methyl-2-propynyl.

Examples of the cyano C₁ -C₆ alkyl represented by R¹¹ and R¹² includecyanomethyl.

Examples of the C₂ -C₈ alkoxyalkyl represented by R¹¹ and R¹² includemethoxymethyl and ethoxyethyl.

Examples of the C₂ -C₈ alkylthioalkyl represented by R¹¹ and R¹² includemethylthiomethyl and methylthioethyl.

Examples of the carboxy C₁ -C₆ alkyl represented by R¹¹ and R¹² includecarboxymethyl and 1-carboxyethyl.

Examples of the (C₁ -C₆ alkoxy)carbonyl C₁ -C₆ alkyl represented by R¹¹and R¹² include methoxycarbonylmethyl, ethoxycarbonylmethyl,propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl,isobutoxycarbonylmethyl, t-butoxycarbonylmethyl, amyloxycarbonylmethyl,isoamyloxycarbonylmethyl, t-amyloxycarbonylmethyl,1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-propoxycarbonylethyl,1-isopropoxycarbonylethyl, 1-butoxycarbonylethyl,1-isobutoxycarbonylethyl, 1-t-butoxycarbonylethyl,1-amyloxycarbonylethyl, 1-isoamyloxycarbonylethyl, and1-t-amyloxycarbonylethyl.

Examples of the {(C₁ -C₄ alkoxy) C₁ -C₄ alkoxy}carbonyl C₁ -C₆ alkylrepresented by R¹¹ and R¹² include methoxymethoxycarbonylmethyl and1-methoxymethoxycarbonylethyl.

Examples of the C₁ -C₆ alkyl represented by R¹³ include methyl, ethyl,propyl, butyl, amyl, isopropyl, isobutyl, and isoamyl.

Examples of the C₁ -C₆ haloalkyl represented by R¹³ include2,2,2-trifluoroethyl, chloromethyl, trichloromethyl, and bromomethyl.

Examples of the C₃ -C₇ cycloalkyl represented by R¹³ includecyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

Examples of the C₁ -C₆ alkyl represented by R¹⁴ and R¹⁵ include methyl,ethyl, propyl, butyl, and isopropyl.

Examples of the C₁ -C₆ haloalkyl represented by R¹⁴ and R¹⁵ includetrifluoromethyl, 2,2,2-trifluoroethyl, 2-chloroethyl, chloromethyl, andtrichloromethyl.

Examples of the phenyl optionally substituted by methyl or nitro, whichis represented by R¹⁴ and R¹⁵, include phenyl, p-methylphenyl,2-nitrophenyl, 3-nitrophenyl, and 4-nitrophenyl.

Examples of the C₁ -C₆ alkyl represented by R¹⁶ include methyl, ethyl,propyl, butyl, amyl, isopropyl, isobutyl, t-butyl, isoamyl, and t-amyl.

Examples of the C₁ -C₆ haloalkyl represented by R¹⁶ includechloromethyl, dichloromethyl, bromomethyl, dibromomethyl, 1-chloroethyl,1,1'-dichloroethyl, 1-bromoethyl, and 1,1-dibromoethyl.

Examples of the C₂ -C₆ alkenyl represented by R¹⁶ include vinyl, allyl,1-propenyl, and 1-methyl-2-propenyl.

Examples of the C₂ -C₆ haloalkenyl represented by R¹⁶ include3,3-dichloro-2-propenyl and 3,3-dibromo-2-propenyl.

Examples of the C₂ -C₆ alkynyl represented by R¹⁶ include 2-butynyl.

Examples of the C₂ -C₆ haloalkynyl represented by R¹⁶ include3-bromo-2-propynyl.

Examples of the C₂ -C₈ alkoxyalkyl represented by R¹⁶ includemethoxymethyl, ethoxymethyl, and isopropoxymethyl.

Examples of the hydroxy C₁ -C₆ alkyl represented by R¹⁶ includehydroxymethyl.

Examples of the C₁ -C₆ alkyl represented by R¹⁷ and R¹⁸ include methyl.

Examples of the C₁ -C₃ alkyl represented by R⁴ include methyl.

Examples of the C₁ -C₆ alkyl represented by R⁵ include methyl, ethyl,propyl, butyl, amyl, isopropyl, isobutyl, and isoamyl.

Examples of the C₁ -C₆ haloalkyl represented by R⁵ include2-chloroethyl, 2-bromoethyl, 3-chlorobutyl, 3-bromobutyl,difluoromethyl, and bromodifluoromethyl.

Examples of the C₃ -C₆ alkenyl represented by R⁵ include allyl,1-methyl-2-propenyl, 3-butenyl, 2-butenyl, 3-methyl-2-butenyl, and2-methyl-3-butenyl.

Examples of the C₃ -C₆ haloalkenyl represented by R⁵ include2-chloro-2-propenyl and 3,3-dichloro-2-propenyl.

Examples of the C₃ -C₆ alkynyl represented by R⁵ include propargyl,1-methyl-2-propynyl, 2-butynyl, and 1,1-dimethyl-2-propynyl.

Examples of the C₃ -C₆ haloalkynyl represented by R⁵ include3-iodo-2-propynyl and 3-bromo-2-propynyl.

Examples of the cyano C₁ -C₆ alkyl represented by R⁵ includecyanomethyl.

Examples of the C₂ -C₈ alkoxyalkyl represented by R⁵ includemethoxymethyl, ethoxymethyl, and 1-methoxyethyl.

Examples of the C₃ -C₈ alkoxyalkoxyalkyl represented by R⁵ includemethoxyethoxymethyl.

Examples of the carboxy C₁ -C₆ alkyl represented by R⁵ includecarboxymethyl, 1-carboxyethyl, and 2-carboxyethyl.

Examples of the (C₁ -C₆ alkoxy)carbonyl C₁ -C₆ alkyl represented by R⁵include methoxycarbonylmethyl, ethoxycarbonylmethyl,propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl,isobutoxycarbonylmethyl, t-butoxycarbonylmethyl, amyloxycarbonylmethyl,isoamyloxycarbonylmethyl, t-amyloxycarbonylmethyl,1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-propoxycarbonylethyl,1-isopropoxycarbonylethyl, 1-butoxycarbonylethyl,1-isobutoxycarbonylethyl, 1-t-butoxycarbonylethyl,1-amyloxycarbonylethyl, 1-isoamyloxycarbonylethyl, and1-t-amyloxycarbonylethyl.

Examples of the {(C₁ ---C₄ alkoxy) C₁ -C₄ alkoxy}carbonyl C₁ -C₆ alkylrepresented by R⁵ include methoxymethoxycarbonylmethyl and1-methoxymethoxycarbonylethyl.

Examples of the (C₃ -C₈ cycloalkoxy)carbonyl C₁ -C₆ alkyl represented byR⁵ include cyclobutyloxycarbonylmethyl, cyclopentyloxycarbonylmethyl,cyclohexyloxycarbonylmethyl, 1-cyclobutyloxycarbonylethyl,1-cyclopentyloxycarbonylethyl, and 1-cyclohexyloxycarbonylethyl.

Examples of the C₂ -C₈ alkylthioalkyl represented by R⁵ includemethylthiomethyl.

Examples of the C₁ -C₆ alkylsulfonyl represented by R⁵ includemethanesulfonyl, ethanesulfonyl, and isopropylsulfonyl.

Examples of the C₁ -C₆ haloalkylsulfonyl represented by R⁵ includetrifluoromethanesulfonyl, chloromethanesulfonyl,trichloromethanesulfonyl, 2-chloroethanesulfonyl, and2,2,2-trifluoroethanesulfonyl.

Examples of the (C₁ -C₈ alkyl)carbonyl represented by R⁵ include acetyl,ethylcarbonyl, propylcarbonyl, and isopropylcarbonyl.

Examples of the (C₁ -C₈ alkoxy)carbonyl represented by R⁵ includemethoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl,amyloxycarbonyl, isopropoxycarbonyl, isobutoxycarbonyl,t-butoxycarbonyl, isoamyloxycarbonyl, and t-amyloxycarbonyl.

Examples of the hydroxy C₁ -C₆ alkyl represented by R⁵ includehydroxymethyl, hydroxyethyl, and hydroxypropyl.

Examples of the C₁ -C₆ alkyl represented by R⁶ include methyl and ethyl.

Examples of the C₁ -C₆ haloalkyl represented by R⁶ include bromomethyl,dibromomethyl, tribromomethyl, 1-bromoethyl, chloromethyl,dichloromethyl, and trichloromethyl.

Examples of the hydroxy C₁ -C₆ alkyl represented by R⁶ includehydroxymethyl.

Examples of the C₁ -C₆ alkoxy C₁ -C₆ alkyl represented by R⁶ includemethoxymethyl, ethoxymethyl, propoxymethyl, and isopropoxymethyl.

Examples of the C₁ -C₆ alkoxy C₁ -C₆ alkoxy C₁ -C₆ alkyl represented byR⁶ include methoxymethoxymethyl, methoxyethoxymethyl, andethoxymethoxymethyl.

Examples of the (C₁ -C₆ alkyl)carbonyloxy C₁ -C₆ alkyl represented by R⁶include acetyloxymethyl, ethylcarbonyloxymethyl, andisopropylcarbonyloxymethyl.

Examples of the (C₁ -C₆ haloalkyl)carbonyloxy C₁ -C₆ alkyl representedby R⁶ include trifluoroacetyloxymethyl, chloroacetyloxymethyl, andtrichloroacetyloxymethyl.

Examples of the (C₁ -C₆ alkoxy)carbonyl represented by R⁶ includemethoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl,amyloxycarbonyl, isopropoxycarbonyl, isobutoxycarbonyl, andisoamyloxycarbonyl.

Examples of the (C₁ -C₆ alkyl)carbonyl represented by R⁶ includemethylcarbonyl, ethylcarbonyl, and isopropylcarbonyl.

Examples of the C₁ -C₆ alkyl-represented by R⁷ include methyl.

Examples of the C₁ -C₆ alkyl represented by R⁸ include methyl and ethyl.

Examples of the C₁ -C₆ haloalkyl represented by R⁸ include chloromethyl,bromomethyl, and fluoromethyl.

Examples of the C₁ -C₆ hydroxyalkyl represented by R⁸ includehydroxymethyl.

Examples of the C₂ -C₈ alkoxyalkyl represented by R⁸ includemethoxymethyl, ethoxymethyl, isopropoxymethyl, butoxymethyl, andisobutoxymethyl.

Examples of the C₃ -C₁₀ alkoxyalkoxyalkyl represented by R⁸ includemethoxymethoxymethyl, methoxyethoxymethyl, and ethoxymethoxymethyl.

Examples of the (C₁ -C₅ alkyl)carbonyloxy C₁ -C₆ alkyl represented by R⁸include acetyloxymethyl, ethylcarbonyloxymethyl, andisopropylcarbonyloxymethyl.

Examples of the (C₁ -C₆ haloalkyl)carbonyloxy C₁ -C₆ alkyl representedby R⁸ include chloromethylcarbonyloxymethyl.

Examples of the carboxy C₁ -C₆ alkyl represented by R⁸ includecarboxymethyl.

Examples of the (C₁ -C₈)alkoxycarbonyl represented by R⁸ includemethoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl,arnyloxycarbonyl, isopropoxycarbonyl, isobutoxycarbonyl, andisoamyloxycarbonyl.

Examples of the (C₁ -C₆ haloalkoxy)carbonyl represented by R⁸ include2-chloroethoxycarbonyl, 2-bromoethoxycarbonyl, 3-chlorobutoxycarbonyl,1-chloro-2-propoxycarbonyl, 1,3-dichloro-2-propoxycarbonyl,2,2-dichloroethoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl,2,2,2-trichloroethoxycarbonyl, and 2,2,2-tribromoethoxycarbonyl.

Examples of the (C₃ -C₁₀ cycloalkoxy)carbonyl represented by R⁸ includecyclobutyloxycarbonyl, cyclopentyloxycarbonyl, andcyclohexyloxycarbonyl.

Examples of the (C₃ -C₈ alkenyloxy)carbonyl represented by R⁸ includeallyloxycarbonyl and 3-butenyloxycarbonyl.

Examples of the (C₃ -C₈ alkynyloxy)carbonyl represented by R⁸ includepropargyloxycarbonyl, 3-butynyloxycarbonyl, and1-methyl-2-propynyloxycarbonyl.

Examples of the (C₁ -C₆ alkyl)aminocarbonyl represented by R⁸ includemethylaminocarbonyl, ethylarninocarbonyl, and propylaminocarbonyl.

Examples of the di(C₁ -C₆ alkyl)aminocarbonyl represented by R⁸ includedimethylaminocarbonyl, diethylaminocarbonyl, anddiisopropylarinocarbonyl.

Examples of the (C₁ -C₆ alkyl)aminocarbonyloxy C₁ -C₆ alkyl representedby R⁸ include methylaminocarbonyloxymethyl, ethylaminocarbonyloxymethyl,and propylaminocarbonyloxymethyl.

Examples of the di(C₁ -C₆ alkyl)aminocarbonyloxy C₁ -C₆ alkylrepresented by R⁸ include dimethylaminocarbonyloxyalkyl anddiethylaminocarbonyloxyalkyl.

In the present compounds, preferred substituents from the viewpoint oftheir herbicidal activity are as follows:

R¹ is preferably hydrogen;

R² is preferably C₁ -C₃ alkyl substituted with one or more halogenatoms, more preferably methyl substituted with one or more fluorineatoms, or ethyl substituted with one or more fluorine atoms, and mostpreferably trifluoromethyl;

R³ is preferably methyl or ethyl, more preferably methyl;

Q is preferably [Q-1], [Q-2], [Q-3], or [Q-4];

Y is preferably halogen;

Z¹ is preferably oxygen or sulfur;

Z² is preferably oxygen;

B is preferably hydrogen, nitro, --OR¹⁰ , --SR¹⁰ , --NHR¹⁰ , --NHSO₂R¹⁴, --COOR¹³, or --CH₂ CHWCOOR¹³, wherein W is preferably hydrogen orchlorine; R¹⁰ is preferably C₁ -C₆ alkyl, C₃ -C₈ cycloalkyl, C₃ -C₆alkenyl, C₃ -C₆ haloalkenyl, C₃ -C₆ alkynyl, cyano C₁ -C₆ alkyl, or (C₁-C₆ alkoxy)carbonyl C₁ -C₆ alkyl; R¹³ is preferably C₁ -C₆ alkyl; andR¹⁴ is preferably C₁ -C₆ alkyl;

R⁵ is preferably C₁ -C₆ alkyl, C₃ -C₆ alkenyl, or C₃ -C₆ alkynyl;

R⁶ is preferably C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, formyl, hydroxymethyl,C₁ -C₆ alkoxymethyl, C₁ -C₆ alkylcarbonyloxymethyl, or C₁ -C₆alkoxycarbonyl;

R⁷ is preferably hydrogen or methyl; and

R⁸ is preferably methyl, hydroxymethyl, C₁ -C₆ alkoxymethyl, (C₁ -C₅alkyl)carbonyloxymethyl, carboxyl, or (C₁ -C₆ alkoxy)carbonyl.

Preferred examples of the present compounds from the viewpoint of theirherbicidal activity are those which contain the above preferredsubstituents in combination. Among these compounds are more preferredones wherein R² is methyl substituted with one or more fluorine atoms,or ethyl substituted with one or more fluorine atoms.

Among these compounds are more preferred ones wherein R² istrifluoromethyl.

Among these compounds are more preferred ones wherein Q is [Q-1] or[Q-2].

When Q is [Q-1], more preferred compounds are those wherein B is --OR¹⁰or --NHR¹⁰. Among these compounds are more preferred ones wherein when Bis --OR¹⁰ , then R¹⁰ is C₃ -C₆ alkynyl or (C₁ -C₆ alkoxy)carbonyl C₁ -C₆alkyl; or when B is --NHR¹⁰, then R¹⁰ is (C₁ -C₆ alkoxy)carbonyl C₁ -C₆alkyl. Among these compounds are more preferred ones wherein R¹⁰ is C₃-C₄ alkynyl, (C₁ -C₆ alkoxy)carbonylmethyl, or 1-(C₁ -C₆alkoxy)carbonylethyl. Among these compounds are more preferred oneswherein R¹ is hydrogen; R³ is methyl; X is fluorine; and Y is chlorine.

When Q is [Q-2], more preferred compounds are those wherein Z¹ isoxygen; n is 1; R⁴ is hydrogen; and R⁵ is C₃ -C₆ alkynyl. Among thesecompounds are more preferred ones wherein R⁵ is C₃ -C₄ alkynyl. Amongthese compounds are those more preferred ones wherein R¹ is hydrogen; R³is methyl; and X is fluorine.

Particularly preferred compounds are those wherein R¹ is hydrogen; R² istrifluoromethyl; R³ is methyl; Q is [Q-1]; X is fluorine; Y is chlorine;and B is propargyloxy; those wherein R¹ is hydrogen; R² istrifluoromethyl; R³ is methyl; Q is [Q-1]; X is fluorine; Y is chlorine;and B is 1-(ethoxycarbonyl)ethoxy; those wherein R¹ is hydrogen; R² istrifluoromethyl; R³ is methyl; Q is [Q-1]; X is fluorine; Y is chlorine;and B is 1-(methoxycarbonyl)ethoxy; and those wherein R¹ is hydrogen; R²is trifluoromethyl; R³ is methyl; Q is [Q-2]; X is fluorine; Z¹ isoxygen; n is 1; R⁴ is hydrogen; and R⁵ is propargyl.

Some of the present compounds have optical isomers based on the presenceof at least one asymmetric carbon atom, and all of the optical isomersare, of course, included within the scope of the present invention.

The present compounds can be produced by various production processes asdescribed below.

(Production Process 1) ##STR9## wherein R¹, R², R³, Q, and D are asdefined above.

The reaction is usually effected in the presence of a base in a solvent.The reaction temperature is usually in the range of -20° to 150° C.,preferably 0° to 100° C. The reaction time is usually in the range of amoment to 96 hours. The amounts of the reagents to be used in thereaction are usually 1 to 5 moles of compound [3] and usually 1 mole toan excess of the base, per mole of compound [2].

Examples of the solvent which can be used include aliphatic hydrocarbonssuch as hexane, heptane, ligroin, cyclohexane, and petroleum ether;aromatic hydrocarbons such as benzene, toluene, and xylene; ethers suchas diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, andethylene glycol dimethyl ether; nitro compounds such as nitromethane andnitrobenzene; acid amides such as formamide, N,N-dimethylformamide, andacetamide; tertiary amines such as pyridine, triethylamine,diisopropylethylamine, N,N-dimethylaniline, N,N-diethylaniline, andN-methylmorpholine; sulfur compounds such as dimethylsulfoxide andsulforane; alcohols such as methanol, ethanol, ethylene glycol, andisopropanol; ketones such as acetone and methyl isobutyl ketone; andmixtures thereof.

Examples of the base used in the reaction include inorganic bases suchas sodium hydride, potassium hydride, sodium hydroxide, potassiumhydroxide, potassium carbonate, and sodium carbonate; and organic basessuch as triethylamine, diisopropylethylamine, pyridine,4-dimethylaminopyridine, N,N-dimethylaniline, and N,N-diethylaniline.

After completion of the reaction, the reaction mixture is poured intowater and the precipitated crystals are collected by filtration, or thereaction mixture is subjected to ordinary post-treatments such asextraction with an organic solvent and concentration, followed by, ifnecessary, subsequent purification by a technique such as chromatographyor recrystallization. Thus the desired compound of the present inventioncan be isolated.

In the present production process, depending upon the reactionconditions, a compound of the formula: ##STR10## wherein Q, R¹, R², andR³ are as defined above, may be formed as a by-product and can beisolated in the same manner as in the isolation of the above presentcompound. Some of the compounds [7] have herbicidal activity.

(Production Process 2)

This is the production process according to the following scheme:##STR11## wherein R²² is C₁ -C₆ alkyl; R⁵¹ is a substituent other thanhydrogen, which is included in the definition of R⁵ ; and R¹ , R², R³,R⁴, and X are as defined above.

Process for Producing Compound [1-2] from Compound [1-1]

Compound [1-2] can be produced by reacting compound [1-1] with anitrating agent in a solvent.

Nitrating agent: nitric acid or the like

Amount of nitrating agent: 1 to 10 moles per mole of compound [1-1]

Solvent: sulfuric acid or the like

Temperature: --10° C. to room temperature

Time: a moment to 24 hours

Process for Producing Compound [1-3] from Compound [1-2]

Compound [1-3] can be produced by reacting compound [1-2] with acompound of the formula: ##STR12## wherein R⁴ and R²² are as definedabove, in the presence of potassium fluoride in a solvent.

Amount of compound [8]: 1 to 50 moles per mole of compound [ 1-2]

Amount of potassium fluoride: 1 to 50 moles per mole of compound [1-2]

Solvent: 1,4-dioxane or the like

Temperature: room temperature to refluxing temperature under heating

Time: a moment to 96 hours

Process for Producing Compound [1-4] from Compound [1-3]

Compound [1-4] can be produced by reducing compound [1-3] with ironpowder in the presence of an acid in a solvent.

Amount of iron powder: 3 moles to an excess per mole of compound [1-3]

Acid: acetic acid or the like

Amount of acid: 1 to 10 moles

Solvent: water, ethyl acetate, or the like

Temperature: room temperature to refluxing temperature under heating

Time: a moment to 24 hours

Process for Producing Compound [1-5] from Compound [1-4]

Compound [1-5] can be produced by reacting compound [1-4] with acompound of the formula:

    R.sup.51 --D                                               [9]

wherein R⁵¹ and D are as defined above.

The reaction is usually effected in the presence of a base in a solvent.The reaction temperature is usually in the range of -20° to 150° C.,preferably 0° to 50° C. The reaction time is usually in the range of amoment to 48 hours.

The amounts of the reagents to be used in the reaction are usually 1 to3 moles of compound [9] and usually 1 to 5 moles of the base, per moleof compound [1-4].

Examples of the base which can be used include inorganic bases such assodium hydride, potassium hydride, sodium hydroxide, potassiumhydroxide, potassium carbonate, and sodium carbonate; and organic basessuch as triethylamine, diisopropylethylamine, pyridine,4-dimethylaminopyridine, N,N-dimethylaniline, and N,N-diethylaniline.

Examples of the solvent which can be used include aliphatic hydrocarbonssuch as hexane, heptane, ligroin, cyclohexane, and petroleum ether;aromatic hydrocarbons such as benzene, toluene, and xylene; halogenatedhydrocarbons such as chlorobenzene and dichlorobenzene; ethers such asdiethyl ether, diisopropyl ether, dioxane; tetrahydrofuran, and ethyleneglycol dimethyl ether; nitro compounds such as nitrobenzene; acid amidessuch as formamide, N,N-dimethylfornamide, and acetamide; tertiary aminessuch as pyridine, triethylamine, diisopropylethylamine,N,N-dimethylamine, N,N-diethylaniline, and N-methylmorpholine; ketonessuch as acetone and methyl isobutyl ketone; and mixtures thereof.

After completion of the reaction, the reaction mixture is poured intowater, if necessary, and subjected to ordinary post-treatments such asextraction with an organic solvent and concentration, followed by, ifnecessary, subsequent purification by a technique such as columnchromatography or recrystallization. Thus the present compound [1-5] canbe obtained.

The above compound [1-3] can also be produced according to the followingscheme: ##STR13## wherein R¹, R², R³, R⁴, R²², and X are as definedabove.

Process for Producing Compound [1-7] from Compound [1-6]

Compound [1-7] can be produced by reacting compound [1-6] with acompound of the formula: ##STR14## wherein R⁴ and R²² are as definedabove, in the presence of a base in a solvent.

Amount of compound [10]: 1 to 2 moles per mole of compound [1-6]

Base: sodium hydride, potassium carbonate, or the like

Amount of base: 1 to 5 moles per mole of compound [1-6]

Solvent: 1,4-dioxane, N,N-dimethylformamide, or the like

Temperature: 0° to 100° C.

Time: a moment to 24 hours

Process for Producing Compound [1-3] from Compound [1-7]

Compound [1-3] can be produced by reacting compound [1-7] with anitrating agent in a solvent.

Nitrating agent: nitric acid or the like

Amount of nitrating agent: 1 to 10 moles per mole of compound [1-7]

Solvent: sulfuric acid, acetic acid, or the like

Temperature: -10° C. to room temperature

Time: a moment to 24 hours

Process for Producing Compound [1-8] from Compound [1-6]

Compound [1-8] can be produced by reacting compound [1-6] with anitrating agent in a solvent.

Nitrating agent: nitric acid or the like

Amount of nitrating agent: 1 to 10 moles per mole of compound [1-6]

Solvent: sulfuric acid, acetic acid, or the like

Temperature: -10° C. to room temperature

Time: a moment to 24 hours

Process for Producing Compound [1-3] from Compound [1-8]

Compound [1-3] can be produced by reacting compound [1-8] with compound[10] in the presence of a base in a solvent.

Amount of compound [10]: 1 to 2 moles per mole of compound [1-8]

Base: sodium hydride, potassium carbonate, or the like

Amount of base: 1 to 5 moles per mole of compound [1-8]

Solvent: 1,4-dioxane, N,N-dimethylformamide, or the like

Temperature: 0° to 100° C.

Time: a moment to 24 hours

(Production Process 3)

This is the production process according to the following scheme:##STR15## wherein X, R¹, R², R³, R⁵¹, and D are as defined above.

Process for Producing Compound [1-10] from Compound [1-9]

Compound [1-10] can be produced by reducing compound [1-9] with ironpowder in the presence of an acid in a solvent.

Amount of iron powder: 3 moles to an excess per mole of compound [1-9]

Acid: acetic acid or the like

Amount of acid: 1 to 10 moles per mole of compound [1-9]

Solvent: water, ethyl acetate, or the like

Temperature: room temperature to refluxing temperature under heating

Time: a moment to 24 hours

Process for Producing Compound [1-11] from Compound [1-10]

Compound [1-11] can be produced by reacting compound [1-10] with sodiumthiocyanate, potassium thiocyanate, or the like in a solvent, and thenreacting it with bromine or chlorine in a solvent.

Amount of sodium thiocyanate, potassium thiocyanate, or the like: 1 to10 moles per mole of compound [1-10]

Amount of bromine or chlorine: 1 to 10 moles per mole of compound [1-10]

Solvent: aqueous hydrochloric acid, aqueous acetic acid, aqueoussulfuric acid, or the like

Temperature: 0° to 50° C.

Time: a moment to 150 hours

Process for Producing Compound [1-12] from Compound [1-11]

Compound [1-12] can be produced by 1) reacting compound [1-11] withsodium nitrite, potassium nitrite, or the like in a solvent, and then 2)heating it in an acidic solution.

<Reaction 1)>

Amount of sodium nitrite, potassium nitrite, or the like: 1 to 2 molesper mole of compound [1-11]

Solvent: aqueous hydrochloric acid or aqueous sulfuric acid

Temperature: -10° to 10° C.

Time: a moment to 5 hours

<Reaction 2)>

Acidic solution: aqueous hydrochloric acid, aqueous sulfuric acid, orthe like

Temperature: 70° C. to refluxing temperature under heating

Time: a moment to 24 hours

Process for Producing Compound [1-13] from Compound 1-12]

Compound [1-13] can be produced by reacting compound [1-12] withcompound [9] in the presence of a base in a solvent.

Amount of compound [9]: 1 to 3 moles per mole of compound [1-12]

Base: sodium hydride, potassium carbonate, or the like

Amount of base: 1 to 10 moles per mole of compound [1-12]

Solvent: 1,4-dioxane, N,N-dimethylformamide, or the like

Temperature: 0° to 100° C.

Time: a moment to 48 hours

(Production Process 4)

This is the production process according to the following scheme:##STR16## wherein X, R¹, R², R³, and R⁵ are as defined above.

Process for Producing Compound [1-15] from Compound [-14]

Compound [1-15] can be produced by reducing compound [1-14] with ironpowder in the presence of an acid in a solvent.

Amount of iron powder: 3 moles to an excess per mole of compound [1-14]

Acid: acetic acid or the like

Amount of acid: 1 to 10 moles per mole of compound [1-14]

Solvent: water, ethyl acetate, or the like

Temperature: room temperature to refluxing temperature under heating

Time: a moment to 24 hours

Process for Producing Compound [1-16] from Compound 1-15]

Compound [1-16] can be produced by 1) reacting compound [1-15] with anitrite salt in a solvent to form a diazonium salt, and then 2) raisingthe temperature to cause the cyclization of the diazonium salt in asolvent.

<Reaction 1)>

Nitrite salt: sodium nitrite, potassium nitrite, or the like

Amount of nitrite salt: 1 to 2 moles per mole of compound [1-15]

Solvent: aqueous hydrochloric acid, aqueous sulfuric acid, or the like

Temperature: -10° to 10° C.

Time: a moment to 5 hours

<Reaction 2)>

Solvent: aqueous hydrochloric acid, aqueous sulfuric acid, or the like

Temperature: room temperature to 80° C.

Time: a moment to 24 hours

(Production Process 5)

This is the production process according to the following scheme:##STR17## wherein Y¹ is a substituent other than nitro, which isincluded in the definition of Y; R¹⁰¹ is a substituent other thanhydrogen, which is included in the definition of R¹⁰ ; and X, R¹, R²,and R³ are as defined above.

Process for Producing Compound [1-18] from compound [1-17]

Compound [1-18] can be produced by reacting compound [1-17] with anitrating agent in a solvent.

Nitrating agent: nitric acid or the like

Amount of nitrating agent: 1 to 10 moles per mole of compound [1-17]

Solvent: sulfuric acid or the like

Temperature: -10° C. to room temperature

Time: a moment to 24 hours

Process for Producing Compound 1-19] from Compound [1-18]

Compound [1-19] can be produced by reducing compound [1-18] with ironpowder in the presence of an acid in a solvent.

Amount of iron powder: 3 moles to an excess per mole of compound [1-18]

Acid: acetic acid or the like

Amount of acid: 1 to 10 moles per mole of compound [1-18]

Solvent: water, ethyl acetate, or the like

Temperature: room temperature to refluxing temperature under heating

Time: a moment to 24 hours

Process for Producing Compound [1-20] from Compound [1-19]

Compound [1-20] can be produced by 1) reacting compound [1-19] with anitrite salt in a solvent, and then 2) heating it in an acid solution.

<Reaction 1)>

Nitrite salt: sodium nitrite, potassium nitrite, or the like

Amount of nitrite salt: 1 to 2 moles per mole of compound [1-19]

Solvent: aqueous hydrochloric acid, aqueous sulfuric acid, or the like

Temperature: -10° to 10° C.

Time: a moment to 5 hours

<Reaction 2)>

Acidic solution: aqueous hydrochloric acid, aqueous sulfuric acid, orthe like

Temperature: 70° C. to refluxing temperature under heating

Time: a moment to 24 hours

Process for Producing Compound [1-21] from Compound [1-20]

Compound [1-21] can be produced by reacting compound [1-20] with acompound of the formula:

    R.sup.101 --D                                              [11]

or

    (R.sup.101).sub.2 O                                        [12]

wherein R¹⁰¹ and D are as defined above.

The reaction is usually effected in the presence of a base in a solvent.The reaction temperature is usually in the range of -20° to 150° C.,preferably 0° to 50° C. The reaction time is usually in the range of amoment to 48 hours.

The amounts of the reagents to be used in the reaction are usually 1 to3 moles of compound [11]or [12] and usually 1 to 5 moles of the base,per mole of compound [1-20].

Examples of the base which can be used include inorganic bases such assodium hydride, potassium hydride, sodium hydroxide, potassiumhydroxide, potassium carbonate, and sodium carbonate; and organic basessuch as triethylamine, diisopropylethylamine, pyridine,4-dimethylaminopyridine, N,N-dimethylaniline, and N,N-diethylaniline.

Examples of the solvent which can be used include aliphatic hydrocarbonssuch as hexane, heptane, ligroin, cyclohexane, and petroleum ether;aromatic hydrocarbons such as benzene, toluene, and xylene; halogenatedhydrocarbons such as chlorobenzene and dichlorobenzene; ethers such asdiethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and ethyleneglycol dimethyl ether; nitro compounds such as nitrobenzene; acid amidessuch as formamide, N,N-dimethylformamide, and acetamide; tertiary aminessuch as pyridine, triethylamnine, diisopropylethylamine,N,N-dimethylamine, N,N-diethylaniline, and N-methylmorpholine; ketonessuch as acetone and methyl isobutyl ketone; and mixtures thereof.

After completion of the reaction, the reaction mixture is poured intowater, if necessary, and subjected to ordinary post-treatments such asextraction with an organic solvent and concentration, followed by, ifnecessary, subsequent purification by a technique such as columnchromatography or recrystallization. Thus the present compound [1-21]can be obtained.

The above compound [1-20] can also be produced by the following process:##STR18## wherein X, Y¹, R¹, R² and R³ are as defined above.

Process for Producing Compound [1-20] from Compound [1-22]

Compound [1-20] can be produced by deprotecting compound [1-22] in thepresence of hydrogen bromide-acetic acid or sulfuric acid without anysolvent or in a solvent

Amount of hydrogen bromide-acetic acid or sulfuric acid: 1 mole to anexcess per mole of compound [1-22]

Solvent: sulfuric acid, acetic acid, or the like

Temperature: 10° to 100° C.

Time: a moment to 24 hours

(Production Process 6)

This is the production process according to the following scheme:##STR19## wherein R²³ and R²⁴ are independently a substituent includedin the definition of R¹¹ or R¹² ; or --COR¹³, --SO₂ R¹⁴, --SO₂ R¹⁵, or--COOR¹³, wherein R¹³, R¹⁴, and R¹⁵ are as defined above; X, Y¹, R¹ ,R², and R³ areas defined above.

Process for Producing Compound [1-23] from Compound [1-19]

Compound [1-23] can be produced by reacting compound [1-19] with acompound of the formula:

    R.sup.23 --D                                               [13]

or

    (R.sup.23).sub.2 O                                         [14]

wherein R²³ and D are as defined above, in the presence or absence of abase without any solvent or in a solvent.

Amount of compound [13] or [14]: 1 mole to an excess per mole ofcompound 1-19]

Base: organic bases such as pyridine and triethylamiine; and inorganicbases such as potassium carbonate

Amount of base: 1 to 3 moles per mole of compound [1-19]

Solvent: N,N-dimethylfornamide, 1,4-dioxane, or the like

Temperature: 0° to 100° C.

Time: a moment to 24 hours

Process for Producing Compound [1-24] from Compound [1-23]

Compound [1-24] can be produced by reacting compound [1-23]with acompound of the formula:

    R.sup.24 --D                                               [15]

or

    (R.sup.24).sub.2 O                                         [16]

wherein R²⁴ and D are as defined above, in the presence or absence of abase without any solvent or in a solvent.

Amount of compound [15] or [16]: 1 mole to an excess per mole ofcompound [1-23]

Base: organic bases such as pyridine and triethylamine; and inorganicbases such as potassium carbonate

Amount of base: 1 to 3 moles per mole of compound [1-23]

Solvent: N,N-dimethylformamide, 1,4-dioxane, or the like

Temperature: 0° to 100° C.

Time: a moment to 24 hours

(Production Process 7)

This is the production process according to the following scheme:##STR20## wherein X, Y¹, R¹, R², R³, and R¹⁰¹ are as defined above.

Process for Producing Compound [1-25] from compound [1-19]

Compound [1-25) can be produced by 1) reacting compound [1-19] with anitrite salt in a solvent, and then 2) reacting it with potassiumxanthate in a solvent.

<Reaction 1)>

Nitrite salt: sodium nitrite, potassium nitrite, or the like

Amount of nitrite salt: 1 to 2 moles per mole of compound [1-19]

Solvent: aqueous hydrochloric acid, aqueous sulfuric acid, or the like

Temperature: -10° to 10° C.

Time: a moment to 5 hours

<Reaction 2)>

Amount of potassium xanthate: 1 to 2 moles per mole of compound [1-19]

Solvent: aqueous hydrochloric acid, aqueous sulfuric acid, or the like

Temperature: 0° to 100° C.

Time: a moment to 24 hours

(see Org. Syn. Coll., Vol. 3, 809 (1955))

Process for Producing Compound [1-26] from Compound [1-25]

Compound [1-26] can be produced by hydrolyzing compound [1-25] in thepresence of a base in a solvent.

Base: inorganic bases such as potassium carbonate

Amount of base: 1 to 5 moles per mole of compound [1-25]

Solvent: alcohols such as methanol and ethanol, or the like

Temperature: 0° C. to refluxing temperature under heating

Time: a moment to 24 hours

(see Org. Syn. Coll., Vol. 3, 809 (1955))

Process for Producing Compound [1-27] from Compound [1-26]

Compound [1-27] can be produced by reacting compound [1-26] withcompound [11] or [12] in the presence of a base in a solvent.

Amount of compound [11] or [12]: 1 mole to an excess per mole ofcompound [1-26]

Base: inorganic bases such as potassium carbonate; and organic basessuch as triethylamine and pyridine

Amount of base: 1 to 3 moles per mole of compound [1 -26]

Solvent: 1,4-dioxane, N,N-dimethylformamide, or the like

Temperature: 0° to 100° C.

Time: a moment to 24 hours

Compound [1-26] can also be produced by the method according to thefollowing scheme: ##STR21## wherein X, Y¹, R¹, R², and R³ are as definedabove.

Process for Producing Compound [1-28] from Compound [1-17]

Compound [1-28] can be produced by reacting compound [1-17] withchlorosulfonic acid without any solvent or in a solvent.

Amount of chlorosulfonic acid: 1 mole to an excess per mole of compound[1-17]

Solvent: sulfuric acid

Temperature: 0° to 70° C.

Time: a moment to 24 hours

(see Org. Syn. Coll., Vol. 1, 8 (1941))

Process for Producing Compound [1-26] from Compound [1-28]

Compound [1-26] can be produced by reducing compound [1-28] in asolvent.

Reducing agent: zinc, tin chloride, or the like

Amount of reducing agent: 3 moles to an excess per mole of compound[1-28]

Solvent: aqueous acetic acid, aqueous hydrochloric acid, aqueoussulfuric acid, or the like

Temperature: room temperature to 100° C.

Time: a moment to 24 hours

(see U.S. Pat. No. 4,709,049, column 9)

(Production Process 8)

This is the production process according to the following scheme:##STR22## wherein R²⁴¹ is bromine or iodine; and X, Y¹, R¹, R², R³, andR¹³ are as defined above.

Process for Producing Compound [1-29] from Compound [1-19]

Compound [1-29] can be produced by 1) making a diazonium salt fromcompound [1-19] in a solvent, and then 2) reacting it with potassiumiodide or copper (I) bromide in a solvent.

<Reaction 1)>

Diazotizing agent: sodium nitrite, potassium nitrite, or the like

Amount of diazotizing agent: 1 to 2 moles per mole of compound [1-19]

Solvent: aqueous hydrogen bromide, aqueous hydrogen chloride, aqueoussulfuric acid, or the like

Temperature; -10° to 10° C.

Time: a moment to 5 hours

<Reaction 2)>

Amount of potassium iodide or copper (I) bromide: 1 mole to an excessper mole of compound [1-19]

Solvent: aqueous hydrogen bromide, water, or the like

Temperature: 0° to 80° C.

Time: a moment to 24 hours

(see Org. Syn. Coll., Vol. 2, 604 (1943), and ibid.,Vol. 1, 136 (1941))

Process for Producing Compound 1-30] from Compound [1-29]

Compound [1-30] can be produced by reacting compound [1-29] with acompound of the formula:

    R.sup.13 --OH                                              [17]

wherein R¹³ is as defined above, in the presence of a transition metalcatalyst and a base in a solvent under an atmosphere of carbon monoxide.

Catalyst: PdCl₂ (PPh₃)₂ or the like

Amount of catalyst: catalytic amount to 0.5 mole per mole of compound[1-29]

Amount of compound [17]: 1 mole to an excess per mole of compound [1-29]

Base: organic bases such as diethylamine

Amount of base: 1 to 10 moles per mole of compound [1-29]

Solvent: N,N-dimethylformamide or the like

Atmospheric pressure of carbon monoxide: 1 to 150 atm

Temperature: 0° to 100° C.

Time: a moment to 72 hours

(see Bull. Chem. Soc. Jpn., 48 (7), 2075 (1975))

(Production Process 9)

The production process according to the following scheme: ##STR23##wherein R¹³¹ is an substituent other than hydrogen, which is included inthe definition of R¹³ ; and X, Y¹, R¹, R², R³, and R¹⁸ are as definedabove.

Process for Producing Compound [1-31] from Compound [1-29]

Compound [1-31] can be produced by reacting compound [1-29] with sodiumformate or potassium formate in the presence of a transition metalcatalyst in a solvent under an atmosphere of carbon monoxide.

Amount of sodium formate or potassium formate: 1 mole to an excess permole of compound [1-29]

Solvent: N,N-dimethylformamide or the like

Catalyst: PdCl₂ (PPh₃)₂ or the like

Amount of catalyst: catalytic amount to 0.5 mole per mole of compound[1-29]

Atmospheric pressure of carbon monoxide: 1 atm

Temperature: 0° to 100° C.

Time: a moment to 72 hours

(see Bull. Chem. Soc. Jpn., 67, 2329 (1994))

Process for Producing Compound [1-32] from Compound [1-31]

Compound [1-32] can be produced by reacting compound [1-31] with acompound of the formula:

    (C.sub.6 H.sub.5).sub.3 P═CR.sup.18 COOR.sup.131       [ 18]

or

    (C.sub.2 H.sub.5 O).sub.2 P(O)CHR.sup.18 COOR.sup.131      [ 19]

wherein R¹⁸ and R¹³¹ are as defined above, in a solvent, and if compound[19] is used, in the presence of a base.

Amount of compound [18] or [19]: 1 to 5 moles per mole of compound[1-31]

Solvent: tetrahydrofuran, toluene, or the like

Base: sodium hydride or the like

Amount of base: 1 to 5 moles per mole of compound [1-31]

Temperature: 0° to 50° C.

Time: a moment to 24 hours

(Production Process 10)

This is the production process according to the following scheme:##STR24## wherein R¹⁷¹ is C₁ -C₆ alkyl; and X, Y¹, R¹, R², R³, R¹⁸, andR¹³¹ are as defined above.

Process for Producing Compound [1-33] from Compound [1-31]

Compound [1-33] can be produced by reacting compound [1-31] with acompound of the formula:

    R.sup.171 --MgBr                                           [20]

or

    R.sup.171 --Li                                             [21]

wherein R¹⁷¹ is as defined above, in a solvent.

Amount of compound [20] or [21]: 1 to 2 moles per mole of compound[1-31]

Solvent: ether solvents such as tetrahydrofuran

Temperature: -78° C. to room temperature

Time: a moment to 24 hours

Process for Producing Compound [1-34]from Compound [1-33]

Compound [1-34] can be produced by subjecting compound [1-33] tooxidative treatment using chromium (VI) oxide-sulfuric acid, pyridiniumchlorochromate, or the like; oxidation using dimethylsulfoxide-aceticanhydride; or Swern oxidation.

Process for Producing Compound [1-35] from Compound [1-34]

Compound [1-35] can be produced by reacting compound [1-34] with acompound of the formula:

    (C.sub.6 H.sub.5).sub.3 P═CR.sup.18 COOR.sup.131       [ 18]

or

    (C.sub.2 H.sub.5 O).sub.2 P(O)CHR.sup.18 COOR.sup.131      [ 19]

wherein R¹⁸ and R¹³¹ are as defined above, in a solvent, and if compound[19] is used, in the presence of a base.

Amount of compound [18] or [19]: 1 to 5 moles per mole of compound[1-34]

Solvent: tetrahydrofuran, toluene, or the like

Base: sodium hydride or the like

Amount of base: 1 to 5 moles per mole of compound [1-34]

Temperature: 0° to 50° C.

Time: a moment to 24 hours

(Production Process 11)

This is the production process according to the following scheme:##STR25## wherein W² is chlorine or bromine; and X, Y¹, R¹ , R², R³, andR¹³ are as defined above.

Compound [1-36] can be produced by reacting compound [1-19] with t-butylnitrite or t-amyl nitrite; a compound of the formula:

    CuW.sup.2.sub.2                                            [ 22]

wherein W² is as defined above; and a compound of the formula:

    CH.sub.2 ═CHCOOR.sup.13                                [ 23]

wherein R¹³ is as defined above, in a solvent.

Amount of t-butyl nitrite or t-amyl nitrite: 1 to 2 moles per mole ofcompound [1-19]

Amount of compound [22]: 1 to 2 moles per mole of compound [1-19]

Amount of compound [23]: 10 moles to an excess per mole of compound[1-19]

Solvent: acetonitrile or the like

Temperature: 0° to 50° C.

Time: a moment to 24 hours

(see EP 0 649 596, page 11)

(Production Process 12)

This is the production process according to the following scheme:##STR26## wherein X, Y¹, R¹, R², R³, and R¹⁰ are as defined above.

Compound [1-37] can be produced by reacting compound [1-28] with acompound of the formula:

    R.sup.10 --OH                                              [24]

wherein R¹⁰ is as defined above, in the presence of a base without anysolvent or in a solvent.

Amount of compound [24]: 1 mole to an excess per mole of compound [1-28]

Base: organic bases such as triethylamine; and inorganic bases such aspotassium carbonate

Amount of base: 1 to 3 moles per mole of compound [1-28]

Solvent: N,N-dimethylformamide, 1,4-dioxane, or the like

Temperature: 0° to 100° C.

Time: a moment to 24 hours

(Production Process 13)

This is the production process according to the following scheme:##STR27## wherein X, Y¹, R¹, R², R³, R¹, and R¹² are as defined above.

Compound [1-38] can be produced by reacting compound [1-28] with acompound of the formula:

    R.sup.11 (R.sup.12)NH                                      [25]

wherein R¹¹ and R¹² are as defined above, in the presence or absence ofa base without any solvent or in a solvent.

Amount of compound [25]: 1 mole to an excess per mole of compound [1-28]

Base: organic bases such as triethylamine; and inorganic bases such aspotassium carbonate

Amount of base: 1 to 3 moles per mole of compound [1-28]

Solvent: N,N-dimethylformamide, 1,4-dioxane, or the like

Temperature: 0° to 100° C.

Time: a moment to 24 hours

(Production Process 14)

This is the production process according to the following scheme:##STR28## wherein R⁶¹ is a substituent other than methyl, which isincluded in the definition of R⁶ ; and X, Y, R¹, R², and R³ are asdefined above.

Process for Producing Compound [140] from Compound [1-39]

Compound [1-40] can be produced by reacting compound [1-39] with2,3-dichloropropene in the presence of a base in a solvent.

Amount of 2,3-dichloropropene: 1 to 3 moles per mole of compound [1-39]

Base: inorganic bases such as potassium carbonate

Amount of base: 1 to 5 moles per mole of compound [1-39]

Solvent: N,N-dimethylformamide or the like

Temperature: 0° to 100° C.

Time: a moment to 24 hours

Process for Producing Compound [1-41] from Compound 1-40]

Compound [1-41] can be produced by heating compound [1-40] in a solvent.

Solvent: N,N-dimethylformamide, N,N-dimethylaniline, N,N-diethylaniline,m-diisopropylbenzene, or the like

Temperature: 70° to 200° C.

Time: a moment to 24 hours

Process for Producing Compound [1-42] from Compound [1-41]

Compound [1-42] can be produced from compound [1-41] according to themethod in which the methyl group in position 2 on the benzofuran ring isreplaced with another substituent, as described in U.S. Pat. No.5,308,829, columns 2-11.

(Production Process 15)

This is the production process according to the following scheme:##STR29## wherein X, Y, R¹, R², R³, and R⁷ are as defined above.

Process for Producing Compound [1-43] from Compound [1-39]

Compound [1-43] can be produced by reacting compound [1-39] with acompound of the formula:

    CH.sub.2 ═CR.sup.7 CH.sub.2 W.sup.2                    [ 26]

wherein W² and R⁷ are as defined above, in the presence of a base in asolvent.

Amount of compound [26]: 1 to 5 moles per mole of compound [1-39]

Base: inorganic bases such as potassium carbonate

Amount of base: 1 to 5 moles per mole of compound [1-39]

Solvent: N,N-dimethylformamide, 1,4-dioxane, or the like

Temperature: 0° to 100° C.

Time: a moment to 24 hours

Process for Producing Compound [1-44] from Compound [1-43]

Compound [1-44] can be produced by heating compound [1-43] in a solvent.

Solvent: N,N-dimethylaniline, N,N-diethylaniline, m-diisopropylbenzene,or the like

Temperature: 100° to 200° C.

Time: a moment to 24 hours

Process for Producing Compound [1-45] from Compound [1-44]

Compound [1-45] can be produced by heating compound [1-44] in thepresence of an acid in a solvent.

Acid: organic acids such as p-toluenesulfonic acid; and inorganic acidssuch as sulfuric acid

Amount of acid: catalytic amount to 1 mole per mole of compound [1-44]

Solvent: toluene, xylene, or the like

Temperature: 100° to 250° C.

Time: a moment to 24 hours

(Production Process 16)

This is the production process according to the following scheme:##STR30## wherein R⁸¹ is a substituent other than methyl andhydroxymethyl, which is included in the definition of R⁸ ; and X, Y, R¹,R², R³, and R⁷ are as defined above.

Process for Producing Compound [1-46] from Compound [1-44]

Compound [1-46] can be produced by reacting compound [1-44] with aperacid in a solvent.

Peracid: m-chloroperbenzoic acid, peracetic acid, or the like

Amount of peracid: 1 mole to an excess per mole of compound [1-44]

Solvent: halogenated hydrocarbons such as dichloromethane; or organicacids such as acetic acid

Temperature: -20° C. to room temperature

Time: a moment to 24 hours

Process for Producing Compound [1-47] from Compound [1-46]

Compound [1-47] can be produced by reacting compound [1-46] in thepresence of a base in a solvent.

Base: potassium carbonate or the like

Amount of base: 1 to 2 moles per mole of compound [1-46]

Solvent: methanol, ethanol, or the like

Temperature: 0° to 50° C.

Time: a moment to 5 hours

Process for Producing Compound [1-48] from Compound [1-47]

Compound [1-48] can be produced from compound [1-47] according to themethod in which the hydroxyalkyl group in position 2 on thedihydrobenzofuran ring is replaced with another substituent, asdescribed in U.S. Pat. No. 5,411,935, columns 5-10.

Compound [2], which is an intermediate compound for the production ofthe present compounds, can be produced with high efficiency by reactingcompound [5] with compound [6] (hereinafter referred to as intermediateproduction process 1).

The reaction is effected without any solvent or in a solvent. Thereaction temperature is usually in the range of -20° to 150° C.,preferably 0° to 50° C. The reaction time is usually in the range of amoment to 240 hours.

The amounts of the reagents to be used in the reaction, although the,proportion of 1 mole of compound [6] to 1 mole of compound [5] is ideal,can be freely changed depending upon the reaction conditions.

Examples of the solvent which can be used include aliphatic hydrocarbonssuch as hexane, heptane, ligroin, cyclohexane, and petroleum ether;aromatic hydrocarbons such as benzene, toluene, and xylene; halogenatedhydrocarbons such as chloroform, carbon tetrachloride, dichloromethane,dichloroethane, chlorobenzene, and dichlorobenzene; ethers such asdiethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and ethyleneglycol dimethyl ether; nitro compounds such as nitromethane andnitrobenzene; acid amides such as formamide, N,N-dimethylformamide, andacetamide; tertiary amines such as pyridine, triethylamine,diisopropylethylamine, N,N-dimethylaniline, N,N-di-ethylaniline, andN-methylmorpholine; sulfur compounds such as dimethylsulfoxide andsulforane; alcohols such as methanol, ethanol, ethylene glycol, andisopropanol; and mixtures thereof.

After completion of the reaction, the reaction -mixture is poured intowater, if necessary, and subjected to ordinary post-treatments such asextraction with an organic solvent and concentration, or purified by atechnique such as column chromatography or recrystallization. Thus thedesired compound can be isolated.

In the intermediate production process 1, compound [6] can be replacedwith a salt of compound [6] with an organic or inorganic acid (e.g.,acetamidine hydrochloride). The reaction is usually effected in thepresence of a base in a solvent. The reaction temperature is usually inthe range of -20° to 150° C., preferably 0° to 50° C. The reaction timeis usually in the range of a moment to 240 hours.

The amounts of the compounds to be used in the reaction, although theproportion of 1 mole of compound [6] to 1 mole of compound [5] is ideal,can be freely changed depending upon the reaction conditions. The amountof the base is usually 1 mole to a large excess per mole of the salt ofcompound [6].

Examples of the base which can be used include inorganic bases such assodium hydride, potassium hydride, sodium hydroxide, potassiumhydroxide, potassium carbonate, and sodium carbonate; and organic basessuch as triethylamine, diisopropylethylamine, pyridine,4-dimethylaminopyridine, N,N-dimethylaniline, and N,N-diethylaniline.

Examples of the solvent which can be used include aliphatic hydrocarbonssuch as hexane, heptane, ligroin, cyclohexane, and petroleum ether;aromatic hydrocarbons such as benzene, toluene, and xylene; halogenatedhydrocarbons such as chloroform, carbon tetrachloride, dichloromethane,dichloroethane, chlorobenzene, and dichlorobenzene; ethers such asdiethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and ethyleneglycol dimethyl ether; nitro compounds such as nitromethane andnitrobenzene; acid amides such as formamide, N,N-dimethylformnamide, andacetamide; tertiary amines such as pyridine, triethylamine,diisopropylethylamine, N,N-dimethylaniline, N,N-diethylaniline, andN-methylmorpholine; sulfur compounds such as dimethylsulfoxide andsulforane; alcohols such as methanol, ethanol, ethylene glycol, andisopropanol; and mixtures thereof.

After completion of the reaction, the reaction mixture is poured intowater and the precipitated crystals are collected by filtration, or thereaction mixture is subjected to ordinary post-treatments such asextraction with an organic solvent and concentration, followed by, ifnecessary, subsequent purification by a technique such as chromatographyor recrystallization. Thus the desired compound can be isolated.

Compound [2] can also be produced by reacting a compound of the formula:##STR31## wherein Q, R¹, and R¹⁹ are as defined above, with compound [6](hereinafter referred to as intermediate production process 2).

The reaction is effected without any solvent or in a solvent. Thereaction temperature is usually in the range of -20° to 150° C.,preferably 0° to 50° C. The reaction time is usually in the range of amoment to 48 hours.

The amounts of the reagents to be used in the reaction, although theproportion of 1 mole of compound [6] to 1 mole of compound [27] isideal, can be freely changed depending upon the reaction conditions.

Examples of the solvent which can be used include aliphatic hydrocarbonssuch as hexane, heptane, ligroin, cyclohexane, and petroleum ether;aromatic hydrocarbons such as benzene, toluene, and xylene; halogenatedhydrocarbons such as chloroform, carbon tetrachloride, dichloromethane,dichloroethane, chlorobenzene, and dichlorobenzene; ethers such asdiethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and ethyleneglycol dimethyl ether; nitro compounds such as nitromethane andnitrobenzene; acid amides such as formamide, N,N-dimethylformamide, andacetamide; tertiary amines such as pyridine, triethylamine,diisopropylethylamine, N,N-dimethylaniline, N,N-diethylaniline, andN-methylmorpholine; sulfur compounds such as dimethylsulfoxide andsulforane; alcohols such as methanol, ethanol, ethylene glycol, andisopropanol; and mixtures thereof.

After completion of the reaction, the reaction mixture is poured intowater, if necessary, and subjected to ordinary post-treatments such asextraction with an organic solvent and concentration, or under certaincircumstances, the reaction mixture is purified by a technique such aschromatography or recrystallization. Thus the desired compound can beisolated.

In the intermediate production process 2, compound [6] can be replacedwith a salt of compound [6] with an organic or inorganic acid (e.g.,acetamidine hydrochloride). The reaction is usually effected in thepresence of a base in a solvent. The reaction temperature is usually inthe range of -20° to 150° C., preferably 0° to 50° C. The reaction timeis usually in the range of a moment to 72 hours.

The amounts of the compounds to be used in the reaction, although theproportion of 1 mole of compound [6] to 1 mole of compound [27] isideal, can be freely changed depending upon the reaction conditions. Theamount of the base is usually 1 mole to a large excess per mole of thesalt of compound [6].

Examples of the base which can be used include inorganic bases such assodium hydroxide, potassium hydroxide, potassium carbonate, and sodiumcarbonate; and organic bases such as triethylamine,diisopropylethylamine, pyridine, 4-dimethylaminopyridine,N,N-dimethylaniline, and N,N-diethylaniline.

Examples of the solvent which can be used include aliphatic hydrocarbonssuch as hexane, heptane, ligroin, cyclohexane, and petroleum ether;aromatic hydrocarbons such as benzene, toluene, and xylene; halogenatedhydrocarbons such as chloroform, carbon tetrachloride, dichloromethane,dichloroethane, chlorobenzene, and dichlorobenzene; ethers such asdiethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and ethyleneglycol dimethyl ether; nitro compounds such as nitromethane andnitrobenzene; acid amides such as formamide, N,N-dimethylformamide, andacetamide; tertiary amines such as pyridine, triethylamine,diisopropylethylamine, N,N-dimethylaniline, N,N-diethylaniline, andN-methylmorpholine; sulfur compounds such as dimethylsulfoxide andsulforane; alcohols such as methanol, ethanol, ethylene glycol, andisopropanol; and mixtures thereof.

After completion of the reaction, the reaction mixture is poured intowater and the precipitated crystals are collected by filtration, or thereaction mixture is subjected to ordinary post-treatments such asextraction with an organic solvent and concentration, followed by, ifnecessary, subsequent purification by a technique such as chromatographyor recrystallization. Thus the desired compound can be isolated.

Compound [6) can be obtained from commercial sources or can be producedby the method as described in J. Am. Chem. Soc., 78, 6032 (1956).

Compound [5] can be produced, for example, by any of the followingmethods 1 to 4.

(Method 1)

(For compounds wherein R¹ is hydrogen)

In this method, compound [27] wherein R¹ is hydrogen is reacted with acompound of the formula:

    R.sup.20 --D                                               [28]

wherein R²⁰ and D are as defined above.

The reaction can be effected in the presence of a base in a solvent. Thereaction temperature is usually in the range of 0° to 100° C. Thereaction time is usually in the range of a moment to 48 hours.

Examples of the base which can be used include inorganic bases such aspotassium carbonate, sodium carbonate, potassium hydroxide, sodiumhydroxide, and sodium hydride.

Compound [28] includes methyl iodide, methyl bromide, ethyl iodide,ethyl bromide, and isopropyl iodide.

The amounts of the reagents to be used in the reaction are usually 1mole to a large excess of the base and usually 1 to 5 moles of compound[28], per mole of compound [27].

Examples of the solvent which can be used include aliphatic hydrocarbonssuch as hexane, heptane, ligroin, cyclohexane, and petroleum ether;aromatic hydrocarbons such as benzene, toluene, and xylene; ethers suchas diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, andethylene glycol dimethyl ether; acid amides such as formamide,N,N-dimethylformamide, and acetamide; tertiary amines such as pyridine,triethylamine, diisopropylethylamine, N,N-dimethylaniline,N,N-diethylaniline, and N-methylmorpholine; and mixtures thereof.

After completion of the reaction, the reaction mixture is poured intowater and the precipitated crystals are collected by filtration, or thereaction mixture is subjected to ordinary post-treatments such asextraction with an organic solvent and concentration, followed by, ifnecessary, subsequent purification by a technique such as chromatographyor recrystallization. Thus the desired compound can be isolated.

(Method 2)

(For compounds wherein R¹ is any other than hydrogen)

In this method, compound [27] wherein R¹ is C₁ -C₃ alkyl is reacted witha compound of the formula:

    HC(OR.sup.20).sub.3                                        [ 29]

wherein R²⁰ is as defined above, in the presence of an acid catalyst(e.g., p-toluene sulfonic acid).

(Method 3)

This is the production process according to the following scheme:##STR32## wherein Q, R¹, R¹⁹, and R²⁰ are as defined above; and G ischlorine, bromine, or iodine.

The reaction conditions in the respective steps are described, forexample, in JP-A 61-106538/1986.

(Method 4)

This is the production process according to the following scheme:##STR33## wherein Q, R¹, R¹⁹, and R²⁰ are as defined above.

The reaction conditions in the respective steps are described, forexample, in JP-A 61-106538/1986.

Compound [27] can be obtained by reacting a compound of the formula:

    QCH.sub.2 COOR.sup.19                                      [ 34]

wherein Q and R¹⁹ are as defined above, with a compound of the formula:

    R.sup.1 COOR.sup.22                                        [ 37]

wherein R¹ and R²² are as defined above, in the presence of anappropriate base.

The reaction is usually effected in a solvent. The reaction temperatureis usually in the range of -20° to 150° C. The reaction time is usuallyin the range of a moment to 72 hours.

The amounts of the compounds to be used in the reaction are usually 1 to10 moles of compound [37] and usually 1 to 20 moles of the base, permole of compound [34].

Examples of the base which can be used include inorganic bases such assodium hydride and potassium hydride.

Examples of the solvent which can be used include aliphatic hydrocarbonssuch as hexane, heptane, ligroin, cyclohexane, and petroleum ether;aromatic hydrocarbons such as benzene, toluene, and xylene; ethers suchas diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, andethylene glycol dimethyl ether; acid amides such as formamide,N,N-dimethylformamide, and acetamide; tertiary amines such as pyridine,triethylamine, diisopropylethylamine, N,N-dimethylaniline,N,N-diethylaniline, and N-methylmorpholine; and mixtures thereof.

After completion of the reaction, the reaction mixture is poured intowater and made acidic by the addition of a mineral acid such ashydrochloric acid or sulfuric acid, followed by ordinary post-treatmentssuch as extraction with an organic solvent and concentration, and ifnecessary, subsequent purification by a technique such as chromatographyor recrystallization. Thus the desired product can be isolated.

Compound [34] is commercially available, or when the correspondingphenylacetic acid (i.e., QCH₂ COOH) is commercially available, compound[34] can be produced by esterifying this phenylacetic acid according tothe ordinary method. However, when neither compound [34] nor thecorresponding phenylacetic acid is commercially available, they can beproduced, for example, by the following scheme: ##STR34## wherein Q andR¹⁹ are as defined above, and J is chlorine or bromine.

Compound [40] can also be produced by the following scheme: ##STR35##wherein Ph is a phenyl group and Q is as defined above.

(Step a-1) can be conducted according to the method as described inOrganic Synthesis Collective Volume, 1, 514 (1941);

(Step a-2), Jikken Kagaku Koza (4th ed.) 21, edited by the ChemicalSociety of Japan, Maruzen K.K., pp. 89-97;

(Step a-3), Jikken Kagaku Koza (4th ed.) 20, edited by the ChemicalSociety of Japan, Maruzen K.K., pp. 1-10;

(Step a-4) and (Step a-8), Organic Synthesis Collective Volume, 1, 131(1941);

(Step a-5), Jikken Kagaku Koza (4th ed.) 20, edited by the ChemicalSociety of Japan, Maruzen K.K., pp. 10-14;

(Step a-6), Organic Synthesis Collective Volume, 3, 370 (1955) orOrganic Synthesis Collective Volume, 6, 634 (1988);

(Step a-7), Organic Synthesis Collective Volume, 1, 107 (1941);

(Step a-9), Organic Synthesis Collective Volume, 2, 351 (1943); and

(Step a-10), Bull. Chem. Soc. Jpn., 67, 2329 (1994).

Compound [38] is known in, or can be produced according to the method asdescribed in, EP-61741-A; U.S. Pat. No. 4,670,046, U.S. Pat. No.4,770,695, U.S. Pat. No. 4,709,049, U.S. Pat. No. 4,640,707, U.S. Pat.No. 4,720,927, U.S. Pat. No. 5,169,431; and JP-A 63-15678711988.

Some examples of compound [38] can also be produced according to thefollowing scheme: ##STR36## wherein R²⁵ is --COR²⁶ or --COOR¹³, R²⁶ ishydrogen or C₁ -C₆ alkyl, and X and Y¹ are as defined above.

The present compounds have excellent herbicidal activity, and some ofthem exhibit excellent selectivity between crop plants and unfavorableweeds. In particular, the present compounds have herbicidal activityagainst various unfavorable weeds as recited below, which may causetrouble in the foliar treatment and soil treatment on upland fields.

Polygonaceae:

wild buckwheat (Polygonum convolvulus), pale smartweed (Polygonumlapathifolium), Pennsylvania smartweed (Polygonum pensylvanicum),ladysthumb (Polygonum persicaria), curly dock (Rumex crispus), broadleafdock (Rumex obtusifolius), Japanese knotweed (Polygonum cuspidatum)

Portulacaceae:

common purslane (Portulaca oleracea)

Caryophyllaceae:

common chickweed (Stellaria media)

Chenopodiaceae:

common lambsquarters (Chenopodium album), kochia (Kochia scoparia)

Amaranthaceae:

redroot pigweed (Amaranthus retroflexus), smooth pigweed (Amaranthushybridus)

Crusiferae:

wild radish (Raphanus raphanistrum), wild mustard (Sinapis arvensis),shepherdspurse (Capsella bursa-pastoris)

Leguminosae:

hemp sesbania (Sesbania exaltata), sicklepod (Cassia obtusifolia),Florida beggarweed (Desmodium tortuosum), white clover (Trifoliumrepens)

Malvaceae:

velvetleaf (Abutilon theophrasti), prickly sida (Sida spinosa)

Violaceae:

field pansy (Viola arvensis), wild pansy (Viola tricolor)

Rubiaceae:

catchweed bedstraw (cleavers) (Galium aparine)

Convolvulaceae:

ivyleaf morningglory (Ipomoea hederacea), tall morningglory (Ipomoeapurpurea), entireleaf morningglory (Ipomoea hederacea var.integriuscula), pitted morningglory (Ipomoea lacunosa), field bindweed(Convolvulus arvensis)

Labiatae:

red deadnettle (Lamium purpureum), henbit (Lamium amplexicaule)

Solanaceae:

jimsonweed (Datura stramonium), black nightshade (Solanum nigrum)

Scrophulariaceae:

birdseye speedwell (Veronica persica), ivyleaf speedwell (Veronicahederaefolia)

Compositae:

common cocklebur (Xanthium pensylvanicum), common sunflower (Helianthusannuus), scentless chamomile (Matricaria perforata or inodora), cornmarigold (Chrysanthemum segetum), pineappleweed (Matricariamatricarioides), common ragweed (Ambrosia artemisiifolia), giant ragweed(Ambrosia trifida), horseweed (Erigeron canadensis), Japanese mugwort(Artemisia princeps), tall goldenrod (Solidago altissima)

Boraginaceae:

field forget-me-not (Myosotis arvensis)

Asclepiadaceae:

common milkweed (Asclepias syriaca)

Euphorbiaceae:

sun spurge (Euphorbia helioscopia), spotted spurge (Euphorbia maculata)

Gramineae:

barnyardgrass (Echinochloa crus-galli), green foxtail (Setaria viridis),giant foxtail (Setaria faberi), large crabgrass (Digitaria sanguinalis),goosegrass (Eleusine indica), annual bluegrass (Poa annua), blackgrass(Alopecurus myosuroides), wild oat (Avena fatua), johnsongrass (Sorghumhalepense), quackgrass (Agropyron repens), downy brome (Bromustectorum), bermudagrass (Cynodon dactylon), fall panicum (Panicumdichotomiflorum), Texas panicum (Panicum texanum), shattercane (Sorghumvulgare)

Commelinaceae:

common dayflower (Commelina communis)

Equisetaceae:

field horsetail (Equisetum arvense)

Cyperaceae:

rice flatsedge (Cyperus iria), purple nutsedge (Cyperus rotundus),yellow nutsedge (Cyperus esculentus)

Furthermore, some of the present compounds have no problematicphytotoxicity on main crops such as corn (Zea mays), wheat (Triticumaestivum), barley (Hordeum vulgare), rice (Oryza sativa), sorghum(Sorghum bicolor), soybean (Glycine max), cotton (Gossypium spp.), sugarbeet (Beta vulgaris), peanut (Arachis hypogaea), sunflower (Helianthusannuus) and canola (Brassica napus); garden crops such as flowers andornamental plants; and vegetable crops.

The present compounds can attain effective control of unfavorable weedsin the no-tillage cultivation of soybean (Glycine max), corn (Zea mays),and wheat (Triticum aestivum). Furthermore, some of them exhibit noproblematic phytotoxicity on crop plants.

The present compounds have herbicidal activity against variousunfavorable weeds as recited below under the flooding treatment on paddyfields.

Gramineae:

barnyardgrass (Echinochloa oryzicola)

Scrophulariaceae:

common falsepimpemel (Lindernia procumbens)

Lythraceae:

Rotala indica, Ammannia multiflora

Elatinaceae:

Elatine triandra

Cyperaceae:

smallflower umbrellaplant (Cyperus difformis), hardstem bulrush (Scirpusjuncoides), needle spikerush (Eleocharis acicularis), Cyperus serotinus,Eleocharis kuroguwai

Pontederiaceae:

Monochoria vaginalis

Alismataceae:

Sagittaria pygmaea, Sagittaria trifolia, Alisma canaliculatum

Potarnogetonaceae:

roundleaf pondweed (Potamogeton distinctus)

Umbelliferae:

Oenanthe javanica

Furthermore, some of the present compounds have no problematicphytotoxicity on transplanted paddy rice.

The present compounds can attain effective control of variousunfavorable weeds in orchards, grasslands, lawns, forests, waterways,canals, or other non-cultivated lands.

The present compounds also have herbicidal activity against variousaquatic plants such as water hyacinth (Eichhornia crassipes), which willgrow in waterways, canals, or the like.

The present compounds have substantially the same characteristics asthose of the herbicidal compounds described in the publication ofInternational Patent Application W095/34659. In the case where cropplants with tolerance imparted by introducing a herbicide tolerance genedescribed in the publication are cultivated, the present compounds canbe used at greater doses than those used when ordinary crop plantswithout tolerance are cultivated, and it is, therefore, possible toattain effective control of other unfavorable plants.

When the present compounds are used as active ingredients of herbicides,they are usually mixed with solid or liquid carriers or diluents,surfactants, and other auxiliary agents to give formulations such asemulsifiable concentrates, wettable powders, flowables, granules,concentrated emulsions, and water-dispersible granules.

These formulations may contain any of the present compounds as an activeingredient at an amount of 0.001% to 80% by weight, preferably 0.005% to70% by weight, based on the total weight of the formulation.

Examples of the solid carrier or diluent may include fine powders orgranules of the following materials: mineral matters such as kaolinclay, attapulgite clay, bentonite, terra alba, pyrophyllite, talc,diatomaceous earth, and calcite; organic substances such as walnut shellpowder; water-soluble organic substances such as urea; inorganic saltssuch as ammonium sulfate; and synthetic hydrated silicon oxide. Examplesof the liquid carrier or diluent may include aromatic hydrocarbons suchas methylnaphthalene, phenylxylylethane, and alkylbenzenes (e.g.,xylene); alcohols such as isopropanol, ethylene glycol, and2-ethoxyethanol; esters such as phthalic acid dialkyl esters; ketonessuch as acetone, cyclohexanone, and isophorone; mineral oils such asmachine oil; vegetable oils such as soybean oil and cotton seed oil;dimethylsulfoxide, N,N-dimethylformamide, acetonitrile,N-methylpyrrolidone, water, and the like.

Examples of the surfactant used for emulsification, dispersing, orspreading may include surfactants of the anionic type, such asalkylsulfates, alkylsulfonates, alkylarylsulfonates,dialkylsulfosuccinates, and phosphates of polyoxyethylene alkyl arylethers; and surfactants of the nonionic type, such as polyoxyethylenealkyl ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylenepolyoxypropylene block copolymers, sorbitan fatty acid esters, andpolyoxyethylene sorbitan fatty acid esters.

Examples of the auxiliary agent used for formulation may includeligninsulfonates, alginates, polyvinyl alcohol, gum arabic,carboxymethyl cellulose (CMC), and isopropyl acid phosphate (PAP).

The present compounds are usually formulated as described above and thenused for the pre- or post-emergence soil, foliar, or flooding treatmentof unfavorable weeds. The soil treatment may include soil surfacetreatment and soil incorporation. The foliar treatment may includeapplication over the plants and directed application in which a chemicalis applied only to the unfavorable weeds so as to keep off the cropplants.

The present compounds can be used, if necessary, in combination withother compounds having herbicidal activity. Examples of the compoundswhich can be used in combination with the present compounds may includevarious compounds described in Catalog 1995 Edition of Farm ChemicalsHandbook (Meister Publishing Company); AG CHEM NEW COMPOUND REVIEW, VOL.13, 1995 (AG CHEM INFORMATION SERVICE); JOSOUZAI KENKYU SOURAN(Hakuyu-sha); or HERBICIDE HANDBOOK Seven Edition (Weed Science Societyof America). Typical examples of such compounds are as follows: atrazin,cyanazine, dimethametryn, metribuzin, prometryn, simazine, simetryn,chlorotoluron, diuron, dymuron, fluometuron, isoproturon, linuron,methabenzthiazuron, bromoxynil, ioxynil, ethalfluralin, pendimethalin,trifluralin, acifluorfen, acifluorfen-sodium, bifenox, chlomethoxynil,fomesafen, lactofen, oxadiazon, oxyfluorfen, carfentrazone,flumiclorac-pentyl, flumioxazine, fluthiacetmethyl, sulfentrazone,thidiazimin, difenzoquat, diquat, paraquat, 2,4-D, 2,4-DB, DCPA, MCPA,MCPB, clomeprop, clopyralid, dicamba, dithiopyr, fluroxypyr, mecoprop,naploanilide, phenothiol, quinclorac, triclopyr, acetochlor, alachlor,butachlor, diethatylethyl, metolachlor, pretilachlor, propachlor,bensulfuron-methyl, chlorsulfuron, chlorimuron-ethyl,halosulfuron-methyl, metsulfuron-methyl, nicosulfuron, primisulfuron,pyrazosulfuron-ethyl, sulfometuron-methyl, thifensulfuronmethyl,triasulfuron, tribenuron-methyl, azimsulfuron, cloransulam-methyl,cyclosulfamuron, flumeturam, flupyrsulfuron, flazasulfuron,imazosulfuron, metosulam, prosulfuron, rimsulfuron,triflusulfuron-methyl, imazamethabenz-methyl, imazapyr, imazaquin,imazethapyr, imazameth, imazamox, bispyribac-sodium, pyriminobac-methyl,pyrithiobac-sodium, alloxydim-sodium, clethodim, sethoxydim,tralkoxydim, diclofop-methyl, fenoxaprop-ethyl, fenoxaprop-p-ethyl,fluazifop-butyl, fluazifop-p-butyl, haloxyfop-methyl,quizalofop-p-ethyl, cyhalofop-butyl, clodinafop-propargyl, benzofenap,clomazone, diflufenican, norflurazon, pyrazolate, pyrazoxyfen,isoxaflutole, sulcotrione, glufosinate-ammonium, glyphosate, bentazon,benthiocarb, bromobutide, butamifos, butylate, dimepiperate,dimethenamid, DSMA, EPTC, esprocarb, isoxaben, mefenacet, molinate,MSMA, piperophos, pributycarb, propanil, pyridate, triallate,cafenstrol, flupoxam, and thiafluamide.

In some cases, the present compounds may be used in combination withother herbicides to enhance their herbicidal activity. Furthermore, thepresent compounds can also be used in combination with insecticides,acaricides, nematocides, fungicides, plant growth regulators,fertilizers, soil improver, or the like.

When the present compounds are used as active ingredients of herbicides,the application amount is usually in the range of 0.01 to 10,000 g,preferably 1 to 8000 g, per hectare, although it may vary depending uponthe weather conditions, formulation type, application timing,application method, soil conditions, crop plants, unfavorable weeds, andthe like. In the case of emulsifiable concentrates, wettable powders,flowables, concentrated emulsions, water-dispersible granules, or thelike, the formulation is usually applied at a prescribed amount afterdiluted with water having a volume of about 10 to 1000 liters perhectare, if necessary, with the addition of an adjuvant such as aspreading agent. In the case of granules or some types of flowables, theformulation is usually applied as such without any dilution.

Examples of the adjuvant used, if necessary, may include, in addition tothe surfactants recited above, polyoxyethylene resin acids (esters),ligninsulfonates, abietates, dinaphthylmethanedisulfonates, crop oilconcentrates, and vegetable oils such as soybean oil, corn oil, cottonseed oil, and sunflower oil.

The present compounds can also be used as active ingredients ofharvesting aids such as defoliants and desiccating agents for cotton,and desiccating agents for potato. In these cases, the present compoundsare usually formulated in the same manner as the case where they areused as active ingredients of herbicides, and used alone or incombination with other harvesting aids for foliar treatment before theharvesting of crops.

The present invention will be further illustrated by the followingproduction examples, formulation examples, and test examples; however,the present invention is not limited to these examples.

The following will describe production examples for the presentcompounds, where the present compounds are designated by their compoundnumbers shown in Tables 1 to 5 and the intermediate compounds aredesignated by their compound numbers shown in Tables 6 to 8. For themeasurement of ¹ H--NMR, tetramethylsilane was used as an internalstandard.

PRODUCTION EXAMPLE 1

(1) First, 0.5 g of compound 1-1010 was dissolved in 5 ml ofN,N-dimethylformamide, to which 0.5 g of potassium carbonate and 0.5 mlof methyl iodide were added, and the mixture was stirred at roomtemperature for 15 hours. After completion of the reaction, the reactionmixture was poured into water and extracted with ethyl acetate. Theorganic layer was dried and concentrated. The residue was subjected topreparative thin layer chromatography (using hexane-ethyl acetate 9:1 asan eluent), which afforded 0.1 g of compound 1-340.

¹ H--NMR (60 MHz, CDCl₃): δ (ppm) 3.70 (3 H, s), 6.70-7.05 (2 H, m),7.25-7.65 (1 H, m), 8.00 (1 H, s)

(2) Then, 0.45 g of compound 1-340 was poured into 10 ml of concentratedsulfuric acid at 0° C., to which 0.3 ml of nitric acid (d=1.42) wasadded, and the mixture was stirred at 0° to 5° C. for 1 hour. Aftercompletion of the reaction, the reaction mixture was added to ice water,and the precipitated crystals were collected by filtration. The crystalswere dissolved in ethyl acetate, and the solution was washed with water.The organic layer was dried and concentrated. The residue was subjectedto silica gel chromatography, which afforded 0.45 g of compound 1-346.

¹ H--NMR (250 MHz, CDCl₃): δ (ppm) 3.76 (3 H, s), 7.17 (1H, dd, J=10.0,10.0 Hz), 8.16 (1H, d, J=1.6 Hz), 8.45 (1H, dd, J=7.3, 7.3 Hz)

(3) Then, 1.2 g of compound 1-346 was dissolved in 10 ml of1,4-di-oxane, to which 1.0 g of potassium fluoride and 1.0 ml of butylglycolate were added, and the mixture was heated under reflux for 24hours. After completion of the reaction, the reaction mixture wasallowed to stand for cooling to room temperature. The reaction mixturewas poured into water and extracted with ethyl acetate. The organiclayer was dried and concentrated. The residue was subjected to silicagel chromatography, which afforded 1.2 g of the present compoundrepresented by the following formula: ##STR37##

(4) Then, 2.0 g of iron powder was added to a mixed solution of 3 ml ofacetic acid and 30 ml of water, followed by heating to 50° C., to whicha solution of 1.2 g of the present compound obtained in the previousstep (3) dissolved in 15 ml of ethyl acetate and 15 ml of acetic acidwas slowly added dropwise. The mixture was stirred at an internaltemperature of 60° to 70° C. for 40 minutes. After completion of thereaction, the reaction mixture was filtered through celite, and thefiltrate was subjected to phase separation with ethyl acetate-aqueoussodium hydrogencarbonate solution. The organic layer was washed withwater, dried, and concentrated, which afforded 1.0 g of compound 2-239,m.p. 194.0° C.

(5) Then, 1.0 g of compound 2-239 was dissolved in 15 ml ofN,N-dimethylformamide, to which 1.6 g of potassium carbonate and 1.0 mlof propargyl bromide were added, and the mixture was stirred at roomtemperature for 1.1/6 hours. After completion of the reaction, thereaction mixture was poured into water and extracted with ethyl acetate.The organic layer was dried and concentrated. The residue was subjectedto silica gel chromatography, followed by recrystallization, whichafforded 0.7 g of compound 2-251.

¹ H--NMR (250 MHz, CDCl₃): δ (ppm) 2.27 (1 H, t, J=2.5 Hz), 3.73 (3 H,s), 4.68 (2 H, s), 4.70 (2 H, d, J=2.5 Hz), 6.86 (1 H, d, J=10.2 Hz),7.40 (1 H, d, J=6.7 Hz), 8.11 (1 H, d, J=1.7 Hz)

Production Example 2

First, 2.0 g of compound 1-1002 was dissolved in 30 ml ofN,N-dimethylformamide, to which 2.17 g of potassium carbonate and 2.0 mlof methyl iodide were added, and the mixture was stirred at roomtemperature for 4 hours. After completion of the reaction, the reactionmixture was poured into water and extracted with ethyl acetate. Theorganic layer was dried and concentrated. The residue was subjected tosilica gel chromatography, which afforded 0.65 g of compound 1-5.

¹ H--NMR (60 MHz, CDCl₃): δ (ppm) 2.40 (3 H, s), 3.60 (3 H, s), 7.35 (2H, d, J=9 Hz), 7.60 (2 H, d, J=9 Hz), 7.90 (1 H, s)

Production Example 3

First, 0.5 g of compound 1-1004 was dissolved in 10 ml ofN,N-dimethylformamide, to which 0.5 g of potassium. carbonate and 0.5 mlof methyl iodide were added, and the mixture was stirred at roomtemperature for 2 hours. After completion of the reaction, the reactionmixture was poured into water and extracted with ethyl acetate. Theorganic layer was dried and concentrated. The residue was subjected tosilica gel chromatography, which afforded 0.1 g of compound 1-10.

¹ H--NMR (60 MHz, CDCl₃): δ (ppm) 2.55 (3 H, s), 3.55 (3 H, s),6.60-7.00 (2 H, m), 7.20-7.50 (1 H, m), 7.85 (1 H, s)

Production Example 4

First, 2.0 g of compound 1-1013 was dissolved in 30 ml ofN,N-dimethylformamide, to which 2.17 g of potassium carbonate and 2.0 mlof methyl iodide were added, and the mixture was stirred at roomtemperature for 90 minutes. After completion of the reaction, thereaction mixture was poured into water and extracted with ethyl acetate.The organic layer was dried and concentrated. The residue wasrecrystallized, which afforded 1.16 g of compound 1-662.

¹ H--NMR (60 MHz, CDCl₃): δ (ppm) 2.60 (3 H, s), 3.60 (3 H, s), 7.30 (2H, m), 7.45 (1 H, m), 7.85 (1 H, s)

Production Example 5

First, 0.3 g of compound 1-1008 was dissolved in 5 ml ofN,N-dimethylformamide, to which 0.3 g of potassium carbonate and 0.3 mlof methyl iodide were added, and the mixture was stirred at roomtemperature for 75 minutes. After completion of the reaction, thereaction mixture was poured into water and extracted with ethyl acetate.The organic layer was dried and concentrated. The residue was subjectedto silica gel chromatography, which afforded 0.1 g of compound 1-335.

¹ H--NMR (60 MHz, CDCl₃): δ (ppm) 3.75 (3 H, s), 7.35 (2 H, d, J=9 Hz),7.60 (2 H, d, J=9 Hz), 8.00 (1 H, s)

The structure of compound 1-335 was also confirmed by X-raycrystallography.

Production Example 6

First, 2.0 g of compound 1-1014 was dissolved in 20 ml ofN,N-dimethylformamide, to which 2.5 g of potassium carbonate and 2.0 mlof methyl iodide were added, and the mixture was stirred at 100° C. for15 hours. After completion of the reaction, the reaction mixture waspoured into water and extracted with ethyl acetate. The organic layerwas washed with saturated sodium chloride solution, dried, andconcentrated. The residue was subjected to silica gel columnchromatography, which afforded 0.9 g of compound 1-476.

¹ H--NMR (250 MHz, CDCl₃): δ (ppm) 1.38 (6 H, d, J=6.1 Hz), 3.73 (3 H,s), 4.50 (1 H, hp, J=6.1 Hz), 7.20 (1 H, d, J=6.6 Hz), 7.23 (1 H, d,J=9.6 Hz), 8.12 (1 H, d, J=1.8 Hz)

Production Example 7

First, 0.7 g of compound 1-476 was poured into 10 ml of concentratedsulfuric acid, and the mixture was stirred at room temperature for 20minutes. After completion of the reaction, the reaction mixture waspoured into water and extracted with ethyl acetate. The organic layerwas washed with saturated sodium chloride solution, dried, andconcentrated. The residue was subjected to silica gel columnchromatography, which afforded 0.5 g of compound 1-391.

¹ H--NMR (300 MHz, CDCl₃): δ (ppm) 3.73 (3 H, s), 5.45 (1 H, s), 7.19 (1H, d, J=9.1 Hz), 7.20 (1 H, d, J=6.5 Hz), 8.07 (1 H, d, J=2 Hz)

Production Example 8

First, 0.3 g of compound 1-391 was dissolved in 5 ml ofN,N-dimethylformamide, to which 0.5 g of potassium carbonate and 0.5 mlof allyl chloride were added, and the mixture was stirred at roomtemperature for 24 hours. After completion of the reaction, the reactionmixture was poured into water and extracted with ethyl acetate. Theorganic layer was washed with saturated sodium chloride solution, dried,and concentrated. The residue was subjected to silica gel columnchromatography, which afforded 0.11 g of compound 1-482.

¹ H--NMR (300 MHz, CDCl₃): δ (ppm) 3.73 (3 H, s), 4.60 (2 H, d, J=5.2Hz), 5.33 (1 H, dd, J=9.5, 1 Hz), 5.45 (1 H, dd, J=16, 1 Hz), 6.06 (1 H,tdd, J=5.2, 16, 9.5 Hz), 7.18 (1 H, d, J=6.4 Hz), 7.24 (1 H, d, J=9.6Hz), 8.11 (1 H, d, J=1.6 Hz)

Production Example 9

First, 0.25 g of compound 1-391 was dissolved in 8 ml ofN,N-dimethylfornamide, to which 0.3 g of potassium carbonate and 0.3 mlof propargyl bromide were added, and the mixture was stirred at roomtemperature for 1.5 hours. After completion of the reaction, thereaction mixture was poured into water and extracted with ethyl acetate.The organic layer was washed with saturated sodium chloride solution,dried, and concentrated. The residue was subjected to silica gelpreparative thin layer chromatography, which afforded 0.25 g of compound1-486.

¹ H--NMR (250 MHz, CDCl₃): δ (ppm) 2.57 (1 H, t, J=2.5 Hz), 3.74 (3 H,s), 4.78 (2 H, d, J=2.5 Hz), 7.26 (1 H, d, J=9.4 Hz), 7.32 (1 H, d,J=6.4 Hz), 8.12 (1 H, d, J=1.7 Hz)

Production Example 10

First, 0.3 g of compound 1-391 was dissolved in 5 ml ofN,N-dimethylformamide, to which 0.5 g of potassium carbonate and 0.5 mlof 3-bromo-1-butyne were added, and the mixture was stirred at roomtemperature for 45 minutes. After completion of the reaction, thereaction mixture was poured into water and extracted with ethyl acetate.The organic layer was washed with saturated sodium chloride solution,dried, and concentrated. The residue was subjected to silica gel columnchromatography, which afforded 0.2 g of compound 1-487.

¹ H--NMR (300 MHz, CDCl₃): δ (ppm) 1.72 (3 H, d, J=6.6 Hz), 2.53 (1 H,d, J=1.9 Hz), 3.73 (3 H, s), 4.86 (1 H, dt, J=1.9, 6.7 Hz), 7.24 (1 H,d, J=9.4 Hz), 7.39 (1 H, d, J=6.5 Hz), 8.11 (1 H, s)

Production Example 11

First, 0.3 g of compound 1-391 was dissolved in 5 ml ofN,N-dimethylformamide, to which 0.5 g of potassium carbonate and 0.5 mlof methyl bromoacetate were added, and the mixture was stirred at roomtemperature for 21 hours. After completion of the reaction, the reactionmixture was poured into water and extracted with ethyl acetate. Theorganic layer was washed with saturated sodium chloride solution, dried,and concentrated. The residue was subjected to silica gel columnchromatography, which afforded 0.32 g of compound 1-495.

¹ H--NMR (300 MHz, CDCl₃): δ (ppm) 3.72 (3 H, s), 3.81 (3 H, s), 4.71 (2H, s), 7.18 (1 H, d, J=6.3 Hz), 7.26 (1 H, d, J=9.4 Hz), 8.11 (1 H, d,J=1.8 Hz)

Production Example 12

First, 0.27 g of compound 1-391 was dissolved in 8 ml ofN,N-dimethylformamide, to which 0.3 g of potassium carbonate and 0.3 mlof ethyl bromoacetate were added, and the mixture was stirred at roomtemperature for 30 minutes. After completion of the reaction, thereaction mixture was poured into water and extracted with ethyl acetate.The organic layer was washed with saturated sodium chloride solution,dried, and concentrated. The residue was subjected to silica gelpreparative thin layer chromatography, which afforded 0.34 g of compound1-496.

¹ H--NMR (300 MHz, CDCl₃): δ (ppm) 1.30 (3 H, t, J=7.1 Hz), 3.72 (3 H,s), 4.27 (2 H, q, J=7.1 Hz), 4.69 (2 H, s), 7.19 (1 H, d, J=6.4 Hz),7.26 (1 H, d, J=9.5 Hz), 8.11 (1 H, d, J=1.7 Hz)

Production Example 13

First, 0.3 g of compound 1-391 was dissolved in 5 ml ofN,N-dimethylformamide, to which 0.5 g of potassium carbonate and 0.5 mlof n-amyl chloroacetate were added, and the mixture was stirred at roomtemperature for 24 hours. After completion of the reaction, the reactionmixture was poured into water and extracted with ethyl acetate. Theorganic layer was washed with saturated sodium chloride solution, dried,and concentrated. The residue was subjected to silica gel columnchromatography, which afforded 0.18 g of compound 1-499.

¹ H--NMR (300 MHz, CDCl₃): δ (ppm) 0.88 (3 H, t, J=6.8 Hz), 1.25-1.45 (4H, m), 1.55-1.70 (2 H, m), 3.72 (3 H, s), 4.19 (2 H, t, J=6.7 Hz), 4.70(2 H, s), 7.18 (1 H, d, J=6.4 Hz), 7.26 (1 H, d, J=9.4 Hz), 8.11 (1 H,s)

Production Example 14

First, 0.3 g of compound 1-391 was dissolved in 5 ml ofN,N-dimethylformamide, to which 0.5 g of potassium carbonate and 0.5 mlof methyl 2-bromopropionate were added, and the mixture was stirred atroom temperature for 23.5 hours. After completion of the reaction, thereaction mixture was poured into water and extracted with ethyl acetate.The organic layer was washed with saturated sodium chloride solution,dried, and concentrated. The residue was subjected to silica gel columnchromatography, which afforded 0.25 g of compound 1-503.

¹ H--NMR (300 MHz, CDCl₃): δ (ppm) 1.67 (3 H, d, J=6.7 Hz), 3.71 (3 H,s), 3.78 (3 H, s), 4.74 (1 H, q, J=6.7 Hz), 7.17 (1 H, d, J=6.4 Hz),7.24 (1 H, d, J=9.8 Hz), 8.09 (1 H, d, J=1.7 Hz)

Production Example 15

First, 0.3 g of compound 1-391 was dissolved in 5 ml ofN,N-dimethylformamide, to which 0.5 g of potassium carbonate and 0.5 mlof ethyl 2-bromopropionate were added, and the mixture was stirred atroom temperature for 20 hours. After completion of the reaction, thereaction mixture was poured into water and extracted with ethyl acetate.The organic layer was washed with saturated sodium chloride solution,dried, and concentrated. The residue was subjected to silica gel columnchromatography, which afforded 0.36 g of compound 1-504.

¹ H--NMR (300 MHz, CDCl₃): δ (ppm) 1.26 (3 H, t, J=7.1 Hz), 1.67 (3 H,d, J=6.7 Hz), 3.71 (3 H, s), 4.23 (2 H, q, J=7.1 Hz), 4.73 (1 H, q,J=6.7 Hz), 7.18 (1 H, d, J=6.4 Hz), 7.24 (1 H, d, J=9.9 Hz), 8.09 (1 H,d, J=2 Hz)

Production Example 16

First, 0.4 g of compound 2-239 was dissolved in 10 ml ofN,N-dimethylformamide, to which 0.4 g of potassium carbonate and 0.4 mlof 3-bromo-1-butyne were added, and the reaction was allowed to proceedat room temperature for 18.5 hours. After completion of the reaction,the reaction mixture was poured into water and extracted with ethylacetate. The organic layer was washed with saturated sodium chloridesolution, dried, and concentrated. The residue was subjected topreparative thin layer chromatography, which afforded 0.11 g of compound2-252.

¹ H--NMR (250 MHz, CDCl₃): δ (ppm) 1.66 (3 H, d, J=7.3 Hz), 2.45 (1 H,d, J=2.6 Hz), 3.74 (3 H, br), 4.60 (1 H, d, J=15.2 Hz), 4.67 (1 H, d,J=15.2 Hz), 6.09 (1 H, dq, J=2.6, 7.3 Hz), 6.87 (1 H, d, J=10.2 Hz),7.89 (1 H, d, J=7.0 Hz), 8.12 (1 H, d, J=1.8 Hz)

Production Example 17

(1) First, 5.5 g of compound 1-1007 was dissolved in 50 ml ofN,N-dimethylformamide, to which 4.0 g of potassium carbonate and 2.5 mlof methyl iodide were added, and the mixture was stirred at roomtemperature for 41/3 hours. After completion of the reaction, thereaction mixture was poured into water and extracted with ethyl acetate.The organic layer was successively washed with water and saturatedsodium chloride solution, dried with magnesium sulfate, andconcentrated. The residue was subjected to silica gel columnchromatography, which afforded 0.16 g of compound 1-334.

¹ H--NMR (250 MHz, CDCl₃): δ (ppm) 3.73 (3 H, s), 7.15 (2 H, dd, J=8.5,8.5 Hz), 7.68 (2 H, dd, J=5.4, 8.5 Hz), 8.70 (1 H, s)

(2) Then, 1.0 g of compound 1-334 was suspended in 15 ml of sulfuricacid at 0° C., to which 0.5 ml of nitric acid (d=1.42) was slowly addeddropwise with stirring, and the mixture was stirred at 5° C. for 1.25hours. After completion of the reaction, the reaction mixture was pouredinto ice water and extracted with ethyl acetate. The organic layer wassuccessively washed with water and saturated sodium chloride solution,dried, and concentrated. The residue was subjected to silica gel columnchromatography, which afforded 1.0 g of compound 1-343.

¹ H--NMR (250 MHz, CDCl₃): δ (ppm) 3.76 (3 H, s), 7.40 (1 H, dd, J=8.7,10.4 Hz), 8.00 (1 H, ddd, J=2.4, 6.5, 8.7 Hz), 8.17 (1 H, s), 8.46 (1 H,dd, J=7.1, 2.4 Hz)

(3) Then, 1.0 g of compound 1-343 was dissolved in 10 ml of 1,4-dioxane,to which 1.0 g of potassium fluoride and 0.7 ml of n-butyl glycolatewere added, and the mixture was heated under reflux for 60 hours. Aftercompletion of the reaction, the reaction mixture was poured into waterand extracted with ethyl acetate. The organic layer was washed withsaturated sodium chloride solution, dried, and concentrated. The residuewas subjected to silica gel column chromatography, which afforded 1.0 gof the present compound represented by the following formula: ##STR38##

(4) Then, 1.5 g of iron powder was added to a mixed solution of 2.0 mlof acetic acid and 20 ml of water, followed by heating to 50° C., towhich a solution of 1.0 g of the present compound obtained in theprevious step (3) dissolved in 15 ml of ethyl acetate and 15 ml ofacetic acid was slowly added dropwise, and the mixture was stirred at aninternal temperature of 50° C. for 25 minutes. After completion of thereaction, the reaction mixture was filtered through celite, and thefiltrate was subjected to phase separation with ethyl acetate-saturatedaqueous sodium hydrogencarbonate solution. The organic layer wassuccessively washed with water and saturated sodium chloride solution,dried, and concentrated. The residue was recrystallized fromhexane-ethyl acetate, which afforded 0.6 g of compound 2-191.

¹ H--NMR (250 MHz, CDCl₃): δ (ppm) 3.73 (3 H, s), 4.66 (2 H, s), 7.05 (1H, d, J=8.4 Hz), 7.22-7.32 (2 H, m), 8.08 (1 H, s)

(5) Then, 0.6 g of compound 2-191 was dissolved in 15 ml ofN,N-dimethylformamide, to which 0.8 g of potassium carbonate and 0.8 mlof propargyl bromide were added, and the mixture was stirred at roomtemperature for 3 hours. After completion of the reaction, the reactionmixture was poured into water and extracted with ethyl acetate. Theorganic layer was washed with saturated sodium chloride solution, dried,and concentrated. The residue was subjected to silica gel columnchromatography, which afforded 0.6 g of compound 2-203.

¹ H--NMR (250 MHz, CDCl₃): δ (ppm) 2.29 (1 H, t, J=2.5 Hz), 3.74 (3 H,s), 4.69 (2 H, s), 4.75 (2 H, d, J=2.5 Hz), 7.09 (1 H, d, J=8.4 Hz),7.36 (1 H, dd, J=2.0, 8.4 Hz), 7.61 (1 H, d, J=2.0 Hz), 8.11 (1 H, s)

Production Example 18

First, 0.3 g of compound 1-391 was dissolved in 5 ml ofN,N-dimethylformamide, to which 0.3 g of potassium carbonate and 0.5 mlof chloroacetonitrile were added, and the mixture was stirred at roomtemperature for 1 hour. After completion of the reaction, the reactionmixture was poured into water and extracted with ethyl acetate. Theorganic layer was washed with saturated sodium chloride solution, dried,and concentrated. The residue was subjected to preparative thin layerchromatography, which afforded 0.3 g of compound 1-491.

¹ H--NMR (250 MHz, CDCl₃): δ (ppm) 3.74 (3 H, s), 4.84 (2 H, s), 7.31 (1H, d, J=9.4 Hz), 7.42 (1 H, d, J=6.3 Hz), 8.16 (1 H, d, J=1.8 Hz)

Production Example 19

First, 2.0 g of iron powder was added to a mixed solution of 5.0 ml ofacetic acid and 50 ml of water, followed by heating to 50° C., to whicha solution of 3.0 g of compound 1-346 in 30 ml of ethyl acetate and 10ml of acetic acid was slowly added dropwise, and the mixture was stirredat an internal temperature of 50° to 60° C. for 30 minutes. Aftercompletion of the reaction, the reaction mixture was filtered throughcelite, and the filtrate was subjected to phase separation with ethylacetate-saturated aqueous sodium hydrogencarbonate solution. The organiclayer was successively washed with water and saturated sodium chloridesolution, dried, and concentrated. The precipitated crystals wererecrystallized from hexane-ethyl acetate, which afforded 2.4 g ofcompound 1-352.

¹ H--NMR (250 MHz, CDCl₃): δ (ppm) 3.67 (2 H, br), 3.72 (3 H, s), 6.89(1 H, dd, J=9.8, 10.6 Hz), 6.96 (1 H, dd, J=7.1, 9.6 Hz), 8.06 (1 H, d,J=1.6 Hz)

Production Example 20

First, 0.8 g of compound 1-352 was dissolved in 8 ml of ethyl2-bromopropionate, and the mixture was stirred at 80° C. for 10 hours.After completion of the reaction, the reaction mixture was poured intowater and extracted with ethyl acetate. The organic layer was washedwith saturated sodium chloride solution, dried, and concentrated. Theresidue was subjected to silica gel column chromatography, whichafforded 0.36 g of compound 1-663.

¹ H--NMR (250 MHz, CDCl₃): δ (ppm) 1.26 (3 H, t, J=7.0 Hz), 1.50 (3 H,d, J=6.9 Hz), 3.72 (3 H, s), 4.04-4.14 (1 H, m), 4.20 (2 H, q, J=7.0Hz), 4.28-4.33 (1 H, m), 6.77 (1 H, dd, J=6.9, 9.4 Hz), 6.90 (1 H, dd,J=9.7, 11.0 Hz), 8.04 (1 H, d, J=1.5 Hz)

Production Example 21

First, 9.4 g of compound 1-1015 was dissolved in 100 ml ofN,N-dimethylformamide, to which 10 g of potassium carbonate and 5.0 mlof methyl iodide were added, and the mixture was stirred at 100° C. for10 hours. After completion of the reaction, the reaction mixture waspoured into water and extracted with ethyl acetate. The organic layerwas washed with saturated sodium chloride solution, dried, andconcentrated. The residue was subjected to silica gel columnchromatography, which afforded 1.7 g of compound 1-664.

¹ H--NMR (250 MHz, CDCl₃): δ (ppm) 3.73 (3 H, s), 7.29 (1 H, d, J=8.2Hz), 7.34 (1 H, dd, J=1.8, 8.2 Hz), 7.52 (1 H, d, J=1.8 Hz), 8.00 (1 H,s)

Production Example 22

First, 1.4 g of compound 1-664 was pulverized with a mortar and pouredinto 20 ml of sulfuric acid cooled to 5° C., followed by stirring for 10minutes, to which 1.0 ml of nitric acid (d=1.42) was slowly addeddropwise, and the mixture was further stirred at 5° C. for 1 hour. Aftercompletion of the reaction, the reaction mixture was poured into icewater, and the precipitated crystals were collected by filtration. Thecrystals were dissolved in ethyl acetate, and the solution was washedwith water. The organic layer was washed with saturated sodium chloridesolution, dried, and concentrated, which afforded 1.4 g of compound1-665.

¹ H--NMR (250 MHz, CDCl₃): δ (ppm) 3.75 (3 H, s), 7.73 (1 H, s), 8.00 (1H, s), 8.08 (1 H, s)

Production Example 23

First, 3.0 g of iron powder was added to a mixed solution of 3.0 ml ofacetic acid and 30 ml of water, followed by heating to 50° C., to whicha solution of 1.2 g of compound 1-665 in 10 ml of ethyl acetate and 10ml of acetic acid was slowly added dropwise, and the mixture was stirredat an internal temperature of 70° C. for 25 minutes. After completion ofthe reaction, the reaction mixture was filtered through celite, and thefiltrate was subjected to phase separation with ethyl acetate-saturatedaqueous sodium hydrogencarbonate solution. The organic layer wassuccessively washed with water and saturated sodium chloride solution,dried, and concentrated. The residue was recrystallized fromhexane-ethyl acetate, which afforded 1.0 g of compound 1-666.

¹ H--NMR (250 MHz, CDCl₃): δ (ppm) 3.72 (3 H, br), 4.12 (2 H, br), 6.74(1 H, s), 7.39 (1 H, s), 7.98 (1 H, s)

Production Example 24

First, 1.0 g of compound 1-666 was dissolved in 10 ml of ethyl2-bromopropionate, and the mixture was stirred at 80° C. for 33 hours.After completion of the reaction, the reaction mixture was poured intowater and extracted with ethyl acetate. The organic layer was washedwith saturated sodium chloride solution, dried, and concentrated. Theresidue was successively subjected to silica gel column chromatographyand preparative thin layer chromatography, which afforded 0.25 g ofcompound 1-667.

¹ H--NMR (250 MHz, CDCl₃): δ (ppm) 1.26 (3 H, t, J=7.0 Hz), 1.51 (3 H,d, J=6.9 Hz), 3.73 (3 H, s), 4.10 (1 H, dq, J=7.6, 6.9 Hz), 4.21 (2 H,d, J=7.0 Hz), 4.90 (1 H, d, J=7.6 Hz), 6.52 (1 H, s), 7.41 (1 H, s),7.97 (1 H, s)

Production Example 25

First, 0.5 g of compound 1-666 was dissolved in 5 ml of pyridine, towhich 0.3 ml of methanesulfonyl chloride was added, and the reaction wasallowed to proceed at room temperature for 23 hours. After completion ofthe reaction, the reaction mixture was poured into water and extractedwith ethyl acetate. The organic layer was washed with saturated sodiumchloride solution, dried, and concentrated, after which the pyridine wasremoved by azeotropic distillation with toluene. The residue wassubjected to silica gel column chromatography, which afforded 0.4 g ofcompound 1-668.

¹ H--NMR (250 MHz, CDCl₃): δ (ppm) 3.08 (3 H, s), 3.74 (3 H, s), 6.89 (1H, br), 7.59 (1 H, s), 7.67 (1 H, s), 8.04 (1 H, s)

Production Example 26

First, 25.6 g of compound 1-1011 was dissolved in 200 ml ofN,N-dimethylformamide, to which 40 g of potassium carbonate and 40 ml ofmethyl iodide were added, and the mixture was stirred at 100° C. for6.2/3 hours. After completion of the reaction, the reaction mixture waspoured into water and extracted with ethyl acetate. The organic layerwas washed with saturated sodium chloride solution, dried, andconcentrated. The residue was subjected to silica gel columnchromatography, which afforded 7.0 g of compound 1-341.

¹ H--NMR (300 MHz, CDCl₃): δ (ppm) 3.73 (3 H, s), 7.19-7.26 (2 H, m),7.49 (1 H, dd, J=7.8, 7.8 Hz), 8.08 (1 H, d, J=1.4 Hz)

Production Example 27

First, 7.0 g of compound 1-341 was poured into 100 ml of sulfuric acidat 0° C., to which 3.0 ml of nitric acid (d=1.42) was slowly addeddropwise, and the mixture was stirred at 0° C. for 1.1/3 hours. Aftercompletion of the reaction, the reaction mixture was poured into water,and the precipitated crystals were collected by filtration. The crystalswere dissolved in ethyl acetate, and the solution was washed with water.The organic layer was washed with saturated sodium chloride solution,dried, and concentrated. The crystals were recrystallized fromhexane-ethyl acetate, which afforded 7.6 g of compound 1-347, m.p.135.2° C.

Production Example 28

First, 7.7 g of iron powder was added to a mixed solution of 5.0 ml ofacetic acid and 50 ml of water, followed by heating to 50° C., to whicha solution of 7.7 g of compound 1-347 in 50 ml of ethyl acetate and 50ml of acetic acid was slowly added dropwise, and the mixture was stirredat an internal temperature of 50° to 70° C. for 50 minutes. Aftercompletion of the reaction, the reaction mixture was filtered throughcelite, and the filtrate was subjected to phase separation with ethylacetate-saturated aqueous sodium hydrogencarbonate solution. The organiclayer was successively washed with water and saturated sodium chloridesolution, dried, and concentrated. The precipitated crystals wererecrystallized from hexane-ethyl acetate, which afforded 6.4 g ofcompound 1-353, m.p. 152.7° C.

Production Example 29

First, 0.7 g of compound 1-353 was dissolved in 10 ml of ethyl2-bromopropionate, and the mixture was stirred at 100° C. for 6 hours.After completion of the reaction, the reaction mixture was poured intowater and extracted with ethyl acetate. The organic layer was washedwith saturated sodium chloride solution, dried, and concentrated. Theresidue was subjected to silica gel column chromatography, whichafforded 0.2 g of compound 1-420.

¹ H--NMR (250 MHz, CDCl₃): δ (ppm) 1.26 (3 H, t, J=7.2 Hz), 1.52 (3 H,d, J=6.9 Hz), 3.71 (3 H, s), 4.12 (1 H, br), 4.21 (2 H, q, J=7.2 Hz),4.71 (1 H, br), 6.75 (1 H, d, J=6.5 Hz), 7.17 (1 H, d, J=9.5 Hz), 8.06(1 H, d, J=1.6 Hz)

Production Example 30

First, 0.3 g of compound 1-353 was dissolved in 5 ml of pyridine, towhich 0.5 ml of methanesulfonyl chloride was added, and the mixture wasstirred at room temperature for 30 minutes. After completion of thereaction, the reaction mixture was poured into water and extracted withethyl acetate. The organic layer was washed with saturated sodiumchloride solution, dried, and concentrated, after which the pyridine wasremoved by azeotropic distillation with toluene. The residue wassubjected to preparative thin layer chromatography, which afforded 0.3 gof compound 1-367.

¹ H--NMR (250 MHz, CDCl₃): δ (ppm) 3.06 (3 H, s), 3.74 (3 H, s), 6.85 (1H, br), 7.30 (1 H, d, J=9.1 Hz), 7.84 (1 H, d, J=6.9 Hz), 8.11 (1 H, d,J=1.4 Hz)

Production Example 31

First, 0.3 g of compound 1-353 was dissolved in 5 ml of pyridine, towhich 5 ml of acetic anhydride was added, and the mixture was stirred atroom temperature for 5 hours. After completion of the reaction, toluenewas added to the reaction mixture, which was concentrated. Theprecipitated crystals were recrystallized from hexane-ethyl acetate,which afforded 0.27 g of compound 1-669.

¹ H--NMR (250 MHz, CDCl₃): δ (ppm) 2.24 (3 H, s), 3.73 (3 H, s), 7.25 (1H, d, J=8.4 Hz), 7.51 (1 H, br), 8.08 (1 H, s), 8.51 (1 H, d, J=7.1 Hz)

Production Example 32

First, 0.18 g of sodium hydride (60% in oil) was suspended in 10 ml ofN,N-dimethylformamide, to which 10 ml of a solution containing 1.0 g ofcompound 1-1014 in N,N-dimethylformamide was added dropwise at 5° C. Thereaction mixture was warmed to room temperature and stirred for 1.5hours, to which 0.5 ml of methyl iodide was added dropwise. The stirringwas further continued at room temperature for 4.5 hours. Aftercompletion of the reaction, the reaction mixture was poured into waterand extracted with ethyl acetate. The organic layer was washed withsaturated sodium chloride solution, dried, and concentrated. The residuewas subjected to silica gel chromatography, which afforded 0.37 g of5-(4-chloro-2-fluoro-5-isopropoxyphenyl)-4-methoxy-2-trifluoromethylpyrimidine,m.p. 77.8° C., and 0.23 g of compound 1-476.

Production Example 33

First, 0.5 ml of t-butyl nitrite, 3.3 ml of ethyl acrylate, and 0.5 g ofcopper (II) chloride were poured into 25 ml of acetonitrile, followed bycooling to 0° C., to which 10 ml of a solution containing 1.0 g ofcompound 1-353 in acetonitrile was slowly added dropwise, and themixture was stirred at 0° C. for 3 hours. After completion of thereaction, the reaction mixture was poured into water and extracted withethyl acetate. The organic layer was washed with saturated sodiumchloride solution, dried, and concentrated. The residue was subjected tosilica gel column chromatography, which afforded 0.5 g of compound1-713.

¹ H--NMR (250 MHz, CDCl₃): δ (ppm) 1.27 (3 H, t, J=7.2 Hz), 3.28 (1 H,dd, J=8.3, 14.2 Hz), 3.52 (1 H, dd, J=6.5, 14.2 Hz), 3.73 (3 H, s), 4.22(1/2×2 H, q, J=7.2 Hz), 4.23 (1/2×2 H, q, J=7.2 Hz), 4.56 (1 H, dd,J=6.5, 8.3 Hz), 7.26 (1 H, d, J=9.7 Hz), 7.51 (1 H, d, J=7.6 Hz), 8.07(1 H, d, J=1.4 Hz)

Production Example 34

First, 0.5 g of compound 1-353 was dissolved in 5 ml of ethylbromoacetate, and the solution was stirred at 100° C. for 9 hours. Aftercompletion of the reaction, the reaction mixture was allowed to standfor cooling to room temperature. The reaction mixture was poured intowater and extracted with ethyl acetate. The organic layer was washedwith saturated sodium chloride solution, dried, and concentrated. Theresidue was subjected to silica gel column chromatography, whichafforded 0.25 g of compound 1-380.

¹ H--NMR (300 MHz, CDCl₃): δ (ppm) 1.30 (3 H, t, J=7.1 Hz), 3.72 (3 H,s), 3.94 (2 H, s), 4.26 (2 H, q, J=7.1 Hz), 4.85 (1 H, br), 6.70 (1 H,d, J=6.5 Hz), 7.18 (1 H, d, J=9.4 Hz), 8.08 (1 H, d, J=1.5 Hz)

Production Example 35

First, 7.5 ml of water and 7.5 ml of concentrated hydrochloric acid wereadded to 2.15 g of compound 1-353, and the mixture was stirred at 50° C.for 1.2/3 hours and then cooled to 5° C., to which a solution of 0.5 gof sodium nitrite in 10 ml of water was slowly added dropwise, and themixture was further stirred at 5° C. for 50 minutes. The solution of adiazonium salt thus formed was added dropwise to a solution of 25 g ofpotassium iodide in 50 ml of water at room temperature, and the mixturewas further stirred at room temperature for 30 minutes. After completionof the reaction, the reaction mixture was poured into water andextracted with ethyl acetate. The organic layer was washed withsaturated sodium chloride solution, dried, and concentrated. The residuewas recrystallized from hexane-ethyl acetate, which afforded 1.93 g ofcompound 1-714, m.p. 156.8° C.

Production Example 36

First, 0.5 g of compound 1-714 was dissolved in 5 ml ofN,N-dimethylformamide, to which 5 ml of ethanol, 1.0 ml of diethylamine,and 0.1 g of dichlorobis(triphenylphosphine)palladium were added, andcarbon monoxide was bubbled into the mixture at room temperature for 13hours. After completion of the reaction, the reaction mixture was pouredinto water and extracted with ethyl acetate. The organic layer waswashed with saturated sodium chloride solution, dried, and concentrated.The residue was subjected to silica gel column chromatography, whichafforded 0.19 g of compound 1-642.

¹ H--NMR (250 MHz, CDCl₃): δ (ppm) 1.40 (3 H, t, J=7.1 Hz), 3.74 (3 H,s), 4.40 (2 H, q, J=7.1 Hz), 7.32 (1 H, d, J=9.6 Hz), 8.10 (1 H, d,J=7.7 Hz), 8.10 (1 H, d, J=1.2 Hz)

Production Example 37

First, 0.9 g of compound 1-714 was dissolved in 10 ml ofN,N-dimethylformamide, to which 2.5 g of sodium formate and a catalyticamount of dichlorobis(triphenylphosphine)palladium were added, andcarbon monoxide was bubbled into the mixture at room temperature for25.5 hours. After completion of the reaction, the reaction mixture waspoured into diluted hydrochloric acid and extracted with ethyl acetate.The organic layer was washed with water and saturated sodium chloridesolution, dried, and concentrated. The residue was subjected to silicagel column chromatography, which afforded 0.22 g of compound 1-656, m.p.158.6° C.

¹ H--NMR (250 MHz, CDCl₃): δ (ppm) 3.74 (3 H, s), 7.33 (1 H, d, J 9.3Hz), 8.09 (1 H, s), 8.12 (1 H, d, J=7.8 Hz), 10.42 (1 H, s)

Production Example 38

First, 0.15 g of compound 1-391 was dissolved in 5 ml ofN,N-dimethylformamide, to which 0.2 g of potassium carbonate and 0.2 mlof cyclopentyl bromide were added, and the reaction was allowed toproceed at room temperature for 21 hours. After completion of thereaction, the reaction mixture was poured into water and extracted withethyl acetate. The organic layer was washed with saturated sodiumchloride solution, dried, and concentrated. The residue was subjected topreparative thin layer chromatography, which afforded 0.14 g of compound1-480, m.p. 101.6° C.

Production Example 39

First, 1.5 g of compound 1-391 was dissolved in 15 ml ofN,N-dimethylformamide, to which 1.5 g of potassium carbonate and 0.7 mlof methallyl chloride were added, and the reaction was allowed toproceed at room temperature for 19 hours. After completion of thereaction, the reaction mixture was poured into water and extracted withethyl acetate. The organic layer was washed with saturated sodiumchloride solution, dried, and concentrated. The resiude was subjected tosilica gel column chromatography, which afforded 0.8 g of compound1-715.

¹ H--NMR (250 MHz, CDCl₃): δ (ppm) 1.85 (3 H, s), 3.73 (3 H, s), 4.49 (2H, s), 5.02 (1 H, d, J=1.3 Hz), 5.14 (1 H, d, J=1.3 Hz), 7.15 (1 H, d,J=6.4 Hz), 7.24 (1 H, d, J=9.3 Hz), 8.11 (1 H, d, J=1.8Hz)

Production Example 40

First, 0.33 g of compound 1-391 was dissolved in 5 ml ofN,N-dimethylformamide, to which 0.23 g of potassium carbonate and 0.3 mlof 2,3-dichloropropene were added, and the reaction was allowed toproceed at room temperature for 1 hour. After completion of thereaction, the reaciton mixture was poured into water and extracted withethyl acetate. The organic layer was washed with saturated sodiumchloride solution, dried, and concentrated. The residue was subjected tothin layer chromatography, which afforded 0.05 g of comound 1-483.

¹ H--NMR (250 MHz, CDCl₃): δ (ppm) 3.74 (3 H, s), 4.64 (2 H, s), 5.49 (1H, d, J=1.1 Hz), 5.66 (1 H, d, J=1.1 Hz), 7.20 (1 H, d, J=6.4 Hz),7.27(1 H, d, J=9.4 Hz), 8.12 (1 H, d, J=1.7 Hz)

Production Example 41

First, 0.33 g of compound 1-391 was dissolved in 5 ml ofN,N-dimethylformamide, to which 0.3 g of potassium carbonate and 0.3 gof chloromethyl ethyl ether were added, and the reaction was allowed toproceed at room temperature for 30 minutes. After completion of thereaction, the reaciton mixture was poured into water and extracted withethyl acetate. The organic layer was washed with saturated sodiumchloride solution, dried, and concentrated. The residue was subjected tothin layer chromatography, which afforded 0.3 g of comound 1-493.

¹ H--NMR (250 MHz, CDCl₃): δ (ppm) 1.24 (3 H, t, J=7.1 Hz), 3.73 (3 H,s), 3.79 (2 H, q, J=7.1 Hz), 5.28 (2 H, s), 7.24 (1 H, d, J=9.36 Hz),7.40 (1 H, d, J=6.6 Hz), 8.09 (1 H, d, J=1.4 Hz)

Production Example 42

First, 0.3 g of compound 1-391 was dissolved in 2 ml ofdimethylsulfoxide, to which 1 ml of acetic anhydride was added, and thereaction was allowed to proceed at room temperature for 18 hours. Aftercompletion of the reaction, the reaciton mixture was poured into waterand extracted with ethyl acetate. The organic layer was washed withsaturated sodium chloride solution, dried, and concentrated. The residuewas subjected to silica gel column chromatography, which afforded 0.13 gof comound 1-494, m.p. 126.8° C.

Some of the present compounds are shown with their compound numbers inTables 1 to 5, where the symbol "n" refers to normal-; "i", iso-; and"c", cyclo-.

                                      TABLE 1                                     __________________________________________________________________________    Compounds of the formula:                                                      ##STR39##                                                                    Compound                                                                      No.    X  Y   R.sup.1                                                                          R.sup.2                                                                           R.sup.3                                                                          B                                                     __________________________________________________________________________    1-1    H  F   H  CH.sub.3                                                                          C.sub.2 H.sub.5                                                                  H                                                     1-2    H  Cl  H  CH.sub.3                                                                          C.sub.2 H.sub.5                                                                  H                                                     1-3    H  Br  H  CH.sub.3                                                                          C.sub.2 H.sub.5                                                                  H                                                     1-4    H  F   H  CH.sub.3                                                                          CH.sub.3                                                                         H                                                     1-5    H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         H                                                     1-6    H  Br  H  CH.sub.3                                                                          CH.sub.3                                                                         H                                                     1-7    F  F   H  CH.sub.3                                                                          C.sub.2 H.sub.5                                                                  H                                                     1-8    F  Cl  H  CH.sub.3                                                                          C.sub.2 H.sub.5                                                                  H                                                     1-9    F  Br  H  CH.sub.3                                                                          C.sub.2 H.sub.5                                                                  H                                                     1-10   F  F   H  CH.sub.3                                                                          CH.sub.3                                                                         H                                                     1-11   F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         H                                                     1-12   F  Br  H  CH.sub.3                                                                          CH.sub.3                                                                         H                                                     1-13   H  F   H  CH.sub.3                                                                          CH.sub.3                                                                         NO.sub.2                                              1-14   H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NO.sub.2                                              1-15   H  Br  H  CH.sub.3                                                                          CH.sub.3                                                                         NO.sub.2                                              1-16   F  F   H  CH.sub.3                                                                          CH.sub.3                                                                         NO.sub.2                                              1-17   F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NO.sub.2                                              1-18   F  Br  H  CH.sub.3                                                                          CH.sub.3                                                                         NO.sub.2                                              1-19   H  F   H  CH.sub.3                                                                          CH.sub.3                                                                         NH.sub.2                                              1-20   H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NH.sub.2                                              1-21   H  Br  H  CH.sub.3                                                                          CH.sub.3                                                                         NH.sub.2                                              1-22   F  F   H  CH.sub.3                                                                          CH.sub.3                                                                         NH.sub.2                                              1-23   F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NH.sub.2                                              1-24   F  Br  H  CH.sub.3                                                                          CH.sub.3                                                                         NH.sub.2                                              1-25   H  F   H  CH.sub.3                                                                          CH.sub.3                                                                         OH                                                    1-26   H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OH                                                    1-27   H  Br  H  CH.sub.3                                                                          CH.sub.3                                                                         OH                                                    1-28   F  F   H  CH.sub.3                                                                          CH.sub.3                                                                         OH                                                    1-29   F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OH                                                    1-30   F  Br  H  CH.sub.3                                                                          CH.sub.3                                                                         OH                                                    1-31   H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.3                                            1-32   H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHC.sub.2 H.sub.5                                     1-33   H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 CH═CH.sub.2                            1-34   H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 C.tbd.CH                                   1-35   H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)C.tbd.CH                                1-36   H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHSO.sub.2 CH.sub.3                                   1-37   H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHSO.sub.2 C.sub.2 H.sub.5                            1-38   H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHSO.sub.2 CH.sub.2 Cl                                1-39   H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHSO.sub.2 CF.sub.3                                   1-40   H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         N(CH.sub.3)SO.sub.2 CH.sub.3                          1-41   H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         N(CH.sub.2 C.tbd.CH)SO.sub.2 CH.sub.3                 1-42   H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCOOCH.sub.3                                         1-43   H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCOOC.sub.2 H.sub.5                                  1-44   H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCOO.sup.n C.sub.3 H.sub.7                           1-45   H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCOO.sup.i C.sub.3 H.sub.7                           1-46   H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCOO.sup.n C.sub.4 H.sub.9                           1-47   H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCOO.sup.n C.sub.5 H.sub.11                          1-48   H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 COOCH.sub.3                                1-49   H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 COOC.sub.2 H.sub.5                         1-50   H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 COO.sup.n C.sub.3 H.sub.7                  1-51   H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 COO.sup.n C.sub.4 H.sub.9                  1-52   H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 COO.sup.n C.sub.5 H.sub.11                 1-53   H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 COO.sup.i C.sub.3 H.sub.7                  1-54   H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 COO.sup.c C.sub.5 H.sub.9                  1-55   H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 COO.sup.c C.sub.6 H.sub.11                 1-56   H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)COOCH.sub.3                             1-57   H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)COOC.sub.2 H.sub.5                      1-58   H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)COO.sup.n C.sub.3 H.sub.7               1-59   H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)COO.sup.n C.sub.4 H.sub.9               1-60   H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)COO.sup.n C.sub.5 H.sub.11              1-61   H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)COO.sup.i C.sub.3 H.sub.7               1-62   H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)COO.sup.c C.sub.5 H.sub.9               1-63   H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)COO.sup.c C.sub.6 H.sub.11              1-64   F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.3                                            1-65   F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHC.sub.2 H.sub.5                                     1-66   F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 CH═CH.sub.2                            1-67   F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 C.tbd.CH                                   1-68   F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)C.tbd.CH                                1-69   F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHSO.sub.2 CH.sub.3                                   1-70   F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHSO.sub.2 C.sub.2 H.sub.5                            1-71   F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHSO.sub.2 CH.sub.2 Cl                                1-72   F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHSO.sub.2 CF.sub.3                                   1-73   F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         N(CH.sub.3)SO.sub.2 CH.sub.3                          1-74   F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         N(CH.sub.2 C.tbd.CH)SO.sub.2 CH.sub.3                 1-75   F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCOOCH.sub.3                                         1-76   F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCOOC.sub.2 H.sub.5                                  1-77   F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCOO.sup.n C.sub.3 H.sub.7                           1-78   F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCOO.sup.i C.sub.3 H.sub.7                           1-79   F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCOO.sup.n C.sub.4 H.sub.9                           1-80   F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCOO.sup.n C.sub.5 H.sub.11                          1-81   F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 COOCH.sub.3                                1-82   F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 COOC.sub.2 H.sub.5                         1-83   F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 COO.sup.n C.sub.3 H.sub.7                  1-84   F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 COO.sup.n C.sub.4 H.sub.9                  1-85   F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 COO.sup.n C.sub.5 H.sub.11                 1-86   F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 COO.sup.i C.sub.3 H.sub.7                  1-87   F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 COO.sup.c C.sub.5 H.sub.9                  1-88   F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NH.sub.2 CH.sub.2 COO.sup.c C.sub.6 H.sub.11          1-89   F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)COOCH.sub.3                             1-90   F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)COOC.sub.2 H.sub.5                      1-91   F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)COO.sup.n C.sub.3 H.sub.7               1-92   F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)COO.sup.n C.sub.4 H.sub.9               1-93   F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)COO.sup.n C.sub.5 H.sub.11              1-94   F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)COO.sup.i C.sub.3 H.sub.7               1-95   F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)COO.sup.c C.sub.5 H.sub.9               1-96   F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)COO.sup.c C.sub.6 H.sub.11              1-97   H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.3                                             1-98   H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OC.sub.2 H.sub.5                                      1-99   H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         O.sup.i C.sub.3 H.sub.7                               1-100  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         O.sup.n C.sub.3 H.sub.7                               1-101  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 CH.sub.2 Cl                                 1-102  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 CF.sub.2 H                                  1-103  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         O.sup.c C.sub.5 H.sub.9                               1-104  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         O.sup.c C.sub.6 H.sub.11                              1-105  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 CH═CH.sub.2                             1-106  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 CCl═CH.sub.2                            1-107  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 CCl═CHCl                                1-108  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)CH═CH.sub.2                          1-109  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 C.tbd.CH                                    1-110  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)C.tbd.CH                                 1-111  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 C.tbd.CBr                                   1-112  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 C.tbd.CCl                                   1-113  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 C.tbd.CCH.sub.2 Cl                          1-114  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 CN                                          1-115  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 OCH.sub.3                                   1-116  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 OC.sub.2 H.sub.5                            1-117  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 SCH.sub.3                                   1-118  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COOCH.sub.3                                 1-119  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COOC.sub.2 H.sub.5                          1-120  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COO.sup.n C.sub.3 H.sub.7                   1-121  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COO.sup.n C.sub.4 H.sub.9                   1-122  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COO.sup.n C.sub.5 H.sub.11                  1-123  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COO.sup.i C.sub.3 H.sub.7                   1-124  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COO.sup.c C.sub.5 H.sub.9                   1-125  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COO.sup.c C.sub.6 H.sub.11                  1-126  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COOCH.sub.3                              1-127  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COOC.sub.2 H.sub.5                       1-128  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COO.sup.n C.sub.3 H.sub.7                1-129  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COO.sup.n C.sub.4 H.sub.9                1-130  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COO.sup.n C.sub.5 H.sub.11               1-131  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COO.sup.i C.sub.3 H.sub.7                1-132  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COO.sup.c C.sub.5 H.sub.9                1-133  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COO.sup.c C.sub.6 H.sub.11               1-134  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 CON(CH.sub.3).sub.2                         1-135  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 CON(C.sub.2 H.sub.5).sub.2                  1-136  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 CON(CH.sub.3)C.sub.2 H.sub.5                1-137  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)CON(CH.sub.3).sub.2                      1-138  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)CON(C.sub.2 H.sub.5).sub.2               1-139  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)CON(CH.sub.3)C.sub.2 H.sub.5             1-140  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COON(CH.sub.3).sub.2                        1-141  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COON(C.sub.2 H.sub.5).sub.2                 1-142  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COON(CH.sub.3).sub.2                     1-143  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COON(C.sub.2 H.sub.5).sub.2              1-144  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.3                                             1-145  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OC.sub.2 H.sub.5                                      1-146  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         O.sup.i C.sub.3 H.sub.7                               1-147  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         O.sup.n C.sub.3 H.sub.7                               1-148  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 CH.sub.2 Cl                                 1-149  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCF.sub.2 CF.sub.2 H                                  1-150  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         O.sup.c C.sub.5 H.sub.9                               1-151  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         O.sup.c C.sub.6 H.sub.11                              1-152  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 CH.sub.2 ═CH.sub.2                      1-153  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 CCl═CH.sub.2                            1-154  F  Cl  H  CH.sub.3                                                                          UH3                                                                              OCH.sub.2 CCl═CHCl                                1-155  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)CH═CH.sub.2                          1-156  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 C.tbd.CH                                    1-157  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)C.tbd.CH                                 1-158  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 C.tbd.CBr                                   1-159  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 C.tbd.CCl                                   1-160  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 C.tbd.CCH.sub.2 Cl                          1-161  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 CN                                          1-162  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 OCH.sub.3                                   1-163  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 OC.sub.2 H.sub.5                            1-164  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 SCH.sub.3                                   1-165  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COOCH.sub.3                                 1-166  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COOC.sub.2 H.sub.5                          1-167  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COO.sup.n C.sub.3 H.sub.7                   1-168  F  CJ  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COO.sup.n C.sub.4 H.sub.9                   1-169  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COO.sup.n C.sub.5 H.sub.11                  1-170  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COO.sup.i C.sub.3 H.sub.7                   1-171  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COO.sup.c C.sub.5 H.sub.9                   1-172  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COO.sup.c C.sub.6 H.sub.11                  1-173  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COOCH.sub.3                              1-174  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COOC.sub.2 H.sub.5                       1-175  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COO.sup.n C.sub.3 H.sub.7                1-176  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COO.sup.n C.sub.4 H.sub.9                1-177  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COO.sup.n C.sub.5 H.sub.11               1-178  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COO.sup.i C.sub.3 H.sub.7                1-179  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COO.sup.c C.sub.5 H.sub.9                1-180  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COO.sup.c C.sub.6 H.sub.11               1-181  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 CON(CH.sub.3).sub.2                         1-182  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 CON(C.sub.2 H.sub.5).sub.2                  1-183  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 CON(CH.sub.3)C.sub.2 H.sub.5                1-184  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)CON(CH.sub.3).sub.2                      1-185  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)CON(C.sub.2 H.sub.5).sub.2               1-186  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)CON(CH.sub.3)C.sub.2 H.sub.5             1-187  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COON(CH.sub.3).sub.2                        1-188  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COON(C.sub.2 H.sub.5).sub.2                 1-189  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COON(CH.sub.3).sub.2                     1-190  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COON(C.sub.2 H.sub.5).sub.2              1-191  H  F   H  CH.sub.3                                                                          CH.sub.3                                                                         SH                                                    1-192  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SH                                                    1-193  H  Br  H  CH.sub.3                                                                          CH.sub.3                                                                         SH                                                    1-194  F  F   H  CH.sub.3                                                                          CH.sub.3                                                                         SH                                                    1-195  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SH                                                    1-196  F  Br  H  CH.sub.3                                                                          CH.sub.3                                                                         SH                                                    1-197  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH.sub.3                                             1-198  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SC.sub.2 H.sub.5                                      1-199  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         S.sup.i C.sub.3 H.sub.7                               1-200  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 CH.sub.2 Cl                                 1-201  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         S.sup.c C.sub.5 H.sub.9                               1-202  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         S.sup.c C.sub.6 H.sub.11                              1-203  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 CH═CH.sub.2                             1-204  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 CCl═CH.sub.2                            1-205  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 CCl═CHCl                                1-206  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)CH═CH.sub.2                          1-207  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 C.tbd.CH                                    1-208  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)C.tbd.CH                                 1-209  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 COOCH.sub.3                                 1-210  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 COOC.sub.2 H.sub.5                          1-211  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 COO.sup.n C.sub.3 H.sub.7                   1-212  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 COO.sup.n C.sub.4 H.sub.9                   1-213  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 COO.sup.n C.sub.5 H.sub.11                  1-214  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 COO.sup.i C.sub.3 H.sub.7                   1-215  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 COO.sup.c C.sub.5 H.sub.9                   1-216  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 COO.sup.c C.sub.6 H.sub.11                  1-217  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)COOCH.sub.3                              1-218  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)COOC.sub.2 H.sub.5                       1-219  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)COO.sup.n C.sub.3 H.sub.7                1-220  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)COO.sup.n C.sub.4 H.sub.9                1-221  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)COO.sup.n C.sub.5 H.sub.11               1-222  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)COO.sup.i C.sub.3 H.sub.7                1-223  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)COO.sup.c C.sub.5 H.sub.9                1-224  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)COO.sup.c C.sub.6 H.sub.11               1-225  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 CON(CH.sub.3).sub.2                         1-226  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 CON(C.sub.2 H.sub.5).sub.2                  1-227  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 CON(tetramethylene)                         1-228  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 CON(pentamethylene)                         1-229  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 CON(ethyleneoxyethylene)                    1-230  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)CON(CH.sub.3).sub.2                      1-231  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)CON(C.sub.2 H.sub.5).sub.2               1-232  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)CON(tetramethylene)                      1-233  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)CON(pentamethylene)                      1-234  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH.sub.3                                             1-235  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SC.sub.2 H.sub.5                                      1-236  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         S.sup.i C.sub.3 H.sub.7                               1-237  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 CH.sub.2 Cl                                 1-238  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         S.sup.c C.sub.5 H.sub.9                               1-239  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         S.sup.c C.sub.6 H.sub.11                              1-240  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 CH═CH.sub.2                             1-241  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 CCl═CH.sub.2                            1-242  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 CCl═CHCl                                1-243  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)CH═CH.sub.2                          1-244  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 C.tbd.CH                                    1-245  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)C.tbd.CH                                 1-246  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 COOCH.sub.3                                 1-247  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 COOC.sub.2 H.sub.5                          1-248  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 COO.sup.n C.sub.3 H.sub.7                   1-249  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 COO.sup.n C.sub.4 H.sub.9                   1-250  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 COO.sup.n C.sub.5 H.sub.11                  1-251  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 COO.sup.i C.sub.3 H.sub.7                   1-252  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 COO.sup.c C.sub.5 H.sub.9                   1-253  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 COO.sup.c C.sub.6 H.sub.11                  1-254  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)COOCH.sub.3                              1-255  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)COOC.sub.2 H.sub.5                       1-256  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)COO.sup.n C.sub.3 H.sub.7                1-257  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)COO.sup.n C.sub.4 H.sub.9                1-258  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)COO.sup.n C.sub.5 H.sub.11               1-259  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)COO.sup.i C.sub.3 H.sub.7                1-260  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)COO.sup.c C.sub.5 H.sub.9                1-261  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)COO.sup.c C.sub.6 H.sub.11               1-262  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 CON(CH.sub.3).sub.2                         1-263  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 CON(C.sub.2 H.sub.5).sub.2                  1-264  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 CON(tetramethylene)                         1-265  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 CON(pentamethylene)                         1-266  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 CON(ethyleneoxyethylene)                    1-267  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)CON(CH.sub.3).sub.2                      1-268  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)CON(C.sub.2 H.sub.5).sub.2               1-269  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)CON(tetramethylene)                      1-270  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)CON(pentamethylene)                      1-271  H  F   H  CH.sub.3                                                                          CH.sub.3                                                                         SO.sub.2 Cl                                           1-272  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SO.sub.2 Cl                                           1-273  H  Br  H  CH.sub.3                                                                          CH.sub.3                                                                         SO.sub.2 Cl                                           1-274  F  F   H  CH.sub.3                                                                          CH.sub.3                                                                         SO.sub.2 Cl                                           1-275  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SO.sub.2 Cl                                           1-276  F  Br  H  CH.sub.3                                                                          CH.sub.3                                                                         SO.sub.2 Cl                                           1-277  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SO.sub.2 OCH.sub.3                                    1-278  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SO.sub.2 OC.sub.2 H.sub.5                             1-279  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SO.sub.2 O.sup.i C.sub.3 H.sub.7                      1-280  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SO.sub.2 OCH.sub.2 CH═CH.sub.2                    1-281  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SO.sub.2 OCH.sub.3                                    1-282  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SO.sub.2 OC.sub.2 H.sub.5                             1-283  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SO.sub.2 O.sup.i C.sub.3 H.sub.7                      1-284  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SO.sub.2 OCH.sub.2 CH═CH.sub.2                    1-285  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SO.sub.2 N(CH.sub.3).sub.2                            1-286  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SO.sub.2 N(C.sub.2 H.sub.5).sub.2                     1-287  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SO.sub.2 N(CH.sub.3).sub.2                            1-288  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         SO.sub.2 N(C.sub.2 H.sub.5).sub.2                     1-289  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         COOH                                                  1-290  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         COOCH.sub.3                                           1-291  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         COOC.sub.2 H.sub.5                                    1-292  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         COO.sup.n C.sub.3 H.sub.7                             1-293  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         COO.sup.n C.sub.4 H.sub.9                             1-294  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         COO.sup.n C.sub.5 H.sub.11                            1-295  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         COO.sup.i C.sub.3 H.sub.7                             1-296  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         COOCH.sub.2 CH.sub.2 Cl                               1-297  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         COOCH.sub.2 CH.sub.2 Br                               1-298  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         CON(CH.sub.3).sub.2                                   1-299  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         CONHCH.sub.3                                          1-300  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         CON(C.sub.2 H.sub.5).sub.2                            1-301  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         CONHC.sub.2 H.sub.5                                   1-302  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         COCH.sub.3                                            1-303  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         COC.sub.2 H.sub.5                                     1-304  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         COCH.sub.2 Cl                                         1-305  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         CHO                                                   1-306  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         CH═CHCOOCH.sub.3                                  1-307  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         CH═CHCOOC.sub.2 H.sub.5                           1-308  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         CH.sub.2 CH.sub.2 COOCH.sub.3                         1-309  H  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         CH.sub.2 CH.sub.2 COOC.sub.2 H.sub.5                  1-310  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         COOH                                                  1-311  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         COOCH.sub.3                                           1-312  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         COOC.sub.2 H.sub.5                                    1-313  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         COO.sup.n C.sub.3 H.sub.7                             1-314  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         COO.sup.n C.sub.4 H.sub.9                             1-315  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         COO.sup.n C.sub.5 H.sub.11                            1-316  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         COO.sup.i C.sub.3 H.sub.7                             1-317  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         COOCH.sub.2 CH.sub.2 Cl                               1-318  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         COOCH.sub.2 CH.sub.2 Br                               1-319  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         CON(CH.sub.3).sub.2                                   1-320  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         CONHCH.sub.3                                          1-321  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         CON(C.sub.2 H.sub.5).sub.2                            1-322  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         CONHC.sub.2 H.sub.5                                   1-323  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         COCH.sub.3                                            1-324  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         COC.sub.2 H.sub.5                                     1-325  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         COCH.sub.2 Cl                                         1-326  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         CHO                                                   1-327  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         CH═CHCOOCH.sub.3                                  1-328  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         CH═CHCOOC.sub.2 H.sub.5                           1-329  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         CH.sub.2 CH.sub.2 COOCH.sub.3                         1-330  F  Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         CH.sub.2 CH.sub.2 COOC.sub.2 H.sub.5                  1-331  H  F   H  CF.sub.3                                                                          C.sub.2 H.sub.5                                                                  H                                                     1-332  H  Cl  H  CF.sub.3                                                                          C.sub.2 H.sub.5                                                                  H                                                     1-333  H  Br  H  CF.sub.3                                                                          C.sub.2 H.sub.5                                                                  H                                                     1-334  H  F   H  CF.sub.3                                                                          CH.sub.3                                                                         H                                                     1-335  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         H                                                     1-336  H  Br  H  CF.sub.3                                                                          CH.sub.3                                                                         H                                                     1-337  F  F   H  CF.sub.3                                                                          C.sub.2 H.sub.5                                                                  H                                                     1-338  F  Cl  H  CF.sub.3                                                                          C.sub.2 H.sub.5                                                                  H                                                     1-339  F  Br  H  CF.sub.3                                                                          C.sub.2 H.sub.5                                                                  H                                                     1-340  F  F   H  CF.sub.3                                                                          CH.sub.3                                                                         H                                                     1-341  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         H                                                     1-342  F  Br  H  CF.sub.3                                                                          CH.sub.3                                                                         H                                                     1-343  H  F   H  CF.sub.3                                                                          CH.sub.3                                                                         NO.sub.2                                              1-344  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NO.sub.2                                              1-345  H  Br  H  CF.sub.3                                                                          CH.sub.3                                                                         NO.sub.2                                              1-346  F  F   H  CF.sub.3                                                                          CH.sub.3                                                                         NO.sub.2                                              1-347  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NO.sub.2                                              1-348  F  Br  H  CF.sub.3                                                                          CH.sub.3                                                                         NO.sub.2                                              1-349  H  F   H  CF.sub.3                                                                          CH.sub.3                                                                         NH.sub.2                                              1-350  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NH.sub.2                                              1-351  H  Br  H  CF.sub.3                                                                          CH.sub.3                                                                         NH.sub.2                                              1-352  F  F   H  CF.sub.3                                                                          CH.sub.3                                                                         NH.sub.2                                              1-353  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NH.sub.2                                              1-354  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)COOCH.sub.3                             1-355  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)COOC.sub.2 H.sub.5                      1-356  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)COO.sup.n C.sub.3 H.sub.7               1-357  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)COO.sup.n C.sub.4 H.sub.9               1-358  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)COO.sup.n C.sub.5 H.sub.11              1-359  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)COO.sup.i C.sub.3 H.sub.7               1-360  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)COO.sup.c C.sub.5 H.sub.9               1-361  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)COO.sup.c C.sub.6 H.sub.11              1-362  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.3                                            1-363  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHC.sub.2 H.sub.5                                     1-364  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 CH═CH.sub.2                            1-365  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 C.tbd.CH                                   1-366  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)C.tbd.CH                                1-367  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHSO.sub.2 CH.sub.3                                   1-368  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHSO.sub.2 C.sub.2 H.sub.5                            1-369  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHSO.sub.2 CH.sub.2 Cl                                1-370  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHSO.sub.2 CF.sub.3                                   1-371  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         N(CH.sub.3)SO.sub.2 CH.sub.3                          1-372  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         N(CH.sub.2 C.tbd.CH)SO.sub.2 CH.sub.3                 1-373  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCOOCH.sub.3                                         1-374  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCOOC.sub.2 H.sub.5                                  1-375  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCOO.sup.n C.sub.3 H.sub.7                           1-376  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCOO.sup.i C.sub.3 H.sub.7                           1-377  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCOO.sup.n C.sub.4 H.sub.9                           1-378  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCOO.sup.n C.sub.5 H.sub.11                          1-379  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 COOCH.sub.3                                1-380  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 COOC.sub.2 H.sub.5                         1-381  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 COO.sup.n C.sub.3 H.sub.7                  1-382  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 COO.sup.n C.sub.4 H.sub.9                  1-383  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 COO.sup.n C.sub.5 H.sub.11                 1-384  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 COO.sup.i C.sub.3 H.sub.7                  1-385  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 COO.sup.c C.sub.5 H.sub.9                  1-386  F  Br  H  CF.sub.3                                                                          CH.sub.3                                                                         NH.sub.2                                              1-387  H  F   H  CF.sub.3                                                                          CH.sub.3                                                                         OH                                                    1-388  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OH                                                    1-389  H  Br  H  CF.sub.3                                                                          CH.sub.3                                                                         OH                                                    1-390  F  F   H  CF.sub.3                                                                          CH.sub.3                                                                         OH                                                    1-391  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OH                                                    1-392  F  Br  H  CF.sub.3                                                                          CH.sub.3                                                                         OH                                                    1-393  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.3                                            1-394  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHC.sub.2 H.sub.5                                     1-395  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 CH═CH.sub.2                            1-396  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 C.tbd.CH                                   1-397  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)C.tbd.CH                                1-398  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHSO.sub.2 CH.sub.3                                   1-399  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHSO.sub.2 C.sub.2 H.sub.5                            1-400  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHSO.sub.2 CH.sub.2 Cl                                1-401  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHSO.sub.2 CF.sub.3                                   1-402  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         N(CH.sub.3)SO.sub.2 CH.sub.3                          1-403  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         N(CH.sub.2 C.tbd.CH)SO.sub.2 CH.sub.3                 1-404  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCOOCH.sub.3                                         1-405  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCOOC.sub.2 H.sub.5                                  1-406  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCOO.sup.n C.sub.3 H.sub.7                           1-407  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCOO.sup.i C.sub.3 H.sub.7                           1-408  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCOO.sup.n C.sub.4 H.sub.9                           1-409  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCOO.sup.n C.sub.5 H.sub.11                          1-410  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 COOCH.sub.3                                1-411  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 COOC.sub.2 H.sub.5                         1-412  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 COO.sup.n C.sub.3 H.sub.7                  1-413  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 COO.sup.n C.sub.4 H.sub.9                  1-414  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 COO.sup.n C.sub.5 H.sub.11                 1-415  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 COO.sup.i C.sub.3 H.sub.7                  1-416  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 COO.sup.c C.sub.5 H.sub.9                  1-417  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 COO.sup.c C.sub.6 H.sub.11                 1-418  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 COO.sup.c C.sub.6 H.sub.11                 1-419  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)COOCH.sub.3                             1-420  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)COOC.sub.2 H.sub.5                      1-421  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)COO.sup.n C.sub.3 H.sub.7               1-422  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)COO.sup.n C.sub.4 H.sub.9               1-423  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)COO.sup.n C.sub.5 H.sub.11              1-424  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)COO.sup.i C.sub.3 H.sub.7               1-425  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)COO.sup.c C.sub.5 H.sub.9               1-426  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)COO.sup.c C.sub.6 H.sub.11              1-427  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.3                                             1-428  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OC.sub.2 H.sub.5                                      1-429  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         O.sup.i C.sub.3 H.sub.7                               1-430  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         O.sup.n C.sub.3 H.sub.7                               1-431  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 CH.sub.2 Cl                                 1-432  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCF.sub.2 CF.sub.2 H                                  1-433  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         O.sup.c C.sub.5 H.sub.9                               1-434  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         O.sup.c C.sub.6 H.sub.11                              1-435  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 CH═CH.sub.2                             1-436  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 CCl═CH.sub.2                            1-437  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 CCl═CHCl                                1-438  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)CH═CH.sub.2                          1-439  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 C.tbd.CH                                    1-440  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)C.tbd.CH                                 1-441  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 C.tbd.CBr                                   1-442  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 C.tbd.CCl                                   1-443  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 C.tbd.CCH.sub.2 Cl                          1-444  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 CN                                          1-445  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 OCH.sub.3                                   1-446  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 OC.sub.2 H.sub.5                            1-447  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 SCH.sub.3                                   1-448  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COOCH.sub.3                                 1-449  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COOC.sub.2 H.sub.5                          1-450  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COO.sup.n C.sub.3 H.sub.7                   1-451  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COO.sup.n C.sub.4 H.sub.9                   1-452  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COO.sup.n C.sub.5 H.sub.11                  1-453  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COO.sup.i C.sub.3 H.sub.7                   1-454  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COO.sup.c C.sub.5 H.sub.9                   1-455  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COO.sup.c C.sub.6 H.sub.11                  1-456  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COOCH.sub.3                              1-457  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COOC.sub.2 H.sub.5                       1-458  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COO.sup.n C.sub.3 H.sub.7                1-459  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COO.sup.n C.sub.4 H.sub.9                1-460  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COO.sup.n C.sub.5 H.sub.11               1-461  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COO.sup.i C.sub.3 H.sub.7                1-462  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COO.sup.c C.sub.5 H.sub.9                1-463  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COO.sup.c C.sub.6 H.sub.11               1-464  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 CON(CH.sub.3).sub.2                         1-465  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 CON(C.sub.2 H.sub.5).sub.2                  1-466  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 CON(CH.sub.3)C.sub.2 H.sub.5                1-467  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)CON(CH.sub.3).sub.2                      1-468  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)CON(C.sub.2 H.sub.5).sub.2               1-469  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)CON(CH.sub.3)C.sub.2 H.sub.5             1-470  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COON(CH.sub.3).sub.2                        1-471  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COON(C.sub.2 H.sub.5).sub.2                 1-472  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COON(CH.sub.3).sub.2                     1-473  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COON(C.sub.2 H.sub.5).sub.2              1-474  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.3                                             1-475  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OC.sub.2 H.sub.5                                      1-476  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         O.sup.i C.sub.3 H.sub.7                               1-477  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         O.sup.n C.sub.3 H.sub.7                               1-478  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 CH.sub.2 Cl                                 1-479  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCF.sub.2 CF.sub.2 H                                  1-480  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         O.sup.c C.sub.5 H.sub.9                               1-481  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         O.sup.c C.sub.6 H.sub.11                              1-482  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 CH.sub.2 ═CH.sub.2                      1-483  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 CCl═CH.sub.2                            1-484  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 CCl═CHCl                                1-485  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)CH═CH.sub.2                          1-486  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 C.tbd.CH                                    1-487  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)C.tbd.CH                                 1-488  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 C.tbd.CBr                                   1-489  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 C.tbd.CCl                                   1-490  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 C.tbd.CCH.sub.2 Cl                          1-491  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 CN                                          1-492  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 OCH.sub.3                                   1-493  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 OC.sub.2 H.sub.5                            1-494  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 SCH.sub.3                                   1-495  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COOCH.sub.3                                 1-496  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COOC.sub.2 H.sub.5                          1-497  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COO.sup.n C.sub.3 H.sub.7                   1-498  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COO.sup.n C.sub.4 H.sub.9                   1-499  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COO.sup.n C.sub.5 H.sub.11                  1-500  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COO.sup.i C.sub.3 H.sub.7                   1-501  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COO.sup.c C.sub.5 H.sub.9                   1-502  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COO.sup.c C.sub.6 H.sub.11                  1-503  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COOCH.sub.3                              1-504  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COOC.sub.2 H.sub.5                       1-505  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COO.sup.n C.sub.3 H.sub.7                1-506  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COO.sup.n C.sub.4 H.sub.9                1-507  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COO.sup.n C.sub.5 H.sub.11               1-508  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COO.sup.i C.sub.3 H.sub.7                1-509  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COO.sup.c C.sub.5 H.sub.9                1-510  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COO.sup.c C.sub.6 H.sub.11               1-511  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 CON(CH.sub.3).sub.2                         1-512  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 CON(C.sub.2 H.sub.5).sub.2                  1-513  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 CON(CH.sub.3)C.sub.2 H.sub.5                1-514  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)CON(CH.sub.3).sub.2                      1-515  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)CON(C.sub.2 H.sub.5).sub.2               1-516  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)CON(CH.sub.3)C.sub.2 H.sub.5             1-517  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COON(CH.sub.3).sub.2                        1-518  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COON(C.sub.2 H.sub.5).sub.2                 1-519  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COON(CH.sub.3).sub.2                     1-520  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COON(C.sub.2 H.sub.5).sub.2              1-521  H  F   H  CF.sub.3                                                                          CH.sub.3                                                                         SH                                                    1-522  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SH                                                    1-523  H  Br  H  CF.sub.3                                                                          CH.sub.3                                                                         SH                                                    1-524  F  F   H  CF.sub.3                                                                          CH.sub.3                                                                         SH                                                    1-525  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SH                                                    1-526  F  Br  H  CF.sub.3                                                                          CH.sub.3                                                                         SH                                                    1-527  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.3                                             1-528  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SC.sub.2 H.sub.5                                      1-529  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         S.sup.i C.sub.3 H.sub.7                               1-530  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 CH.sub.2 Cl                                 1-531  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         S.sup.c C.sub.5 H.sub.9                               1-532  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         S.sup.c C.sub.6 H.sub.11                              1-533  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 CH═CH.sub.2                             1-534  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 CCl═CH.sub.2                            1-535  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 CCl═CHCl                                1-536  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)CH═CH.sub.2                          1-537  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 C.tbd.CH                                    1-538  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)C.tbd.CH                                 1-539  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 COOCH.sub.3                                 1-540  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 COOC.sub.2 H.sub.5                          1-541  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 COO.sup.n C.sub.3 H.sub.7                   1-542  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 COO.sup.n C.sub.4 H.sub.9                   1-543  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 COO.sup.n C.sub.5 H.sub.11                  1-544  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 COO.sup.i C.sub.3 H.sub.7                   1-545  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 COO.sup.c C.sub.5 H.sub.9                   1-546  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 COO.sup.c C.sub.6 H.sub.11                  1-547  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)COOCH.sub.3                              1-548  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)COOC.sub.2 H.sub.5                       1-549  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)COO.sup.n C.sub.3 H.sub.7                1-550  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)COO.sup.n C.sub.4 H.sub.9                1-551  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)COO.sup.n C.sub.5 H.sub.11               1-552  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)COO.sup.i C.sub.3 H.sub.7                1-553  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)COO.sup.c C.sub.5 H.sub.9                1-554  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)COO.sup.c C.sub.6 H.sub.11               1-555  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 CON(CH.sub.3).sub.2                         1-556  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 CON(C.sub.2 H.sub.5).sub.2                  1-557  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 CON(tetramethylene)                         1-558  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 CON(pentamethylene)                         1-559  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 CON(ethyleneoxyethylene)                    1-560  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)CON(CH.sub.3).sub.2                      1-561  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)CON(C.sub.2 H.sub.5).sub.2               1-562  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)CON(tetramethylene)                      1-563  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)CON(pentamethylene)                      1-564  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.3                                             1-565  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SC.sub.2 H.sub.5                                      1-566  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         S.sup.i C.sub.3 H.sub.7                               1-567  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 CH.sub.2 Cl                                 1-568  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         S.sup.c C.sub.5 H.sub.9                               1-569  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         S.sup.c C.sub.6 H.sub.11                              1-570  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 CH═CH.sub.2                             1-571  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 CCl═CH.sub.2                            1-572  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 CCl═CHCl                                1-573  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)CH═CH.sub.2                          1-574  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 C.tbd.CH                                    1-575  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)C.tbd.CH                                 1-576  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 COOCH.sub.3                                 1-577  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 COOC.sub.2 H.sub.5                          1-578  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 COO.sup.n C.sub.3 H.sub.7                   1-579  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 COO.sup.n C.sub.4 H.sub.9                   1-580  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 COO.sup.n C.sub.5 H.sub.11                  1-581  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 COO.sup.i C.sub.3 H.sub.7                   1-582  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 COO.sup.c C.sub.5 H.sub.9                   1-583  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 COO.sup.c C.sub.6 H.sub.11                  1-584  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)COOCH.sub.3                              1-585  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)COOC.sub.2 H.sub.5                       1-586  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)COO.sup.n C.sub.3 H.sub.7                1-587  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)COO.sup.n C.sub.4 H.sub.9                1-588  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)COO.sup.n C.sub.5 H.sub.11               1-589  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)COO.sup.i C.sub.3 H.sub.7                1-590  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)COO.sup.c C.sub.5 H.sub.9                1-591  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)COO.sup.c C.sub.6 H.sub.11               1-592  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 CON(CH.sub.3).sub.2                         1-593  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 CON(C.sub.2 H.sub.5).sub.2                  1-594  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 CON(tetramethylene)                         1-595  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 CON(pentamethylene)                         1-596  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 CON(ethyleneoxyethylene)                    1-597  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)CON(CH.sub.3).sub.2                      1-598  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)CON(C.sub.2 H.sub.5).sub.2               1-599  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)CON(tetramethylene)                      1-600  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)CON(pentamethylene)                      1-601  H  F   H  CF.sub.3                                                                          CH.sub.3                                                                         SO.sub.2 Cl                                           1-602  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SO.sub.2 Cl                                           1-603  H  Br  H  CF.sub.3                                                                          CH.sub.3                                                                         SO.sub.2 Cl                                           1-604  F  F   H  CF.sub.3                                                                          CH.sub.3                                                                         SO.sub.2 Cl                                           1-605  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SO.sub.2 Cl                                           1-606  F  Br  H  CF.sub.3                                                                          CH.sub.3                                                                         SO.sub.2 Cl                                           1-607  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SO.sub.2 OCH.sub.3                                    1-608  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SO.sub.2 OC.sub.2 H.sub.5                             1-609  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SO.sub.2 O.sup.i C.sub.3 H.sub.7                      1-610  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SO.sub.2 OCH.sub.2 CH═CH.sub.2                    1-611  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SO.sub.2 OCH.sub.3                                    1-612  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SO.sub.2 OC.sub.2 H.sub.5                             1-613  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SO.sub.2 O.sup.i C.sub.3 H.sub.7                      1-614  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SO.sub.2 OCH.sub.2 CH═CH.sub.2                    1-615  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SO.sub.2 N(CH.sub.3).sub.2                            1-616  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SO.sub.2 N(C.sub.2 H.sub.5).sub.2                     1-617  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SO.sub.2 N(CH.sub.3).sub.2                            1-618  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SO.sub.2 N(C.sub.2 H.sub.5).sub.2                     1-619  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         COOH                                                  1-620  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         COOCH.sub.3                                           1-621  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         COOC.sub.2 H.sub.5                                    1-622  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         COO.sup.n C.sub.3 H.sub.7                             1-623  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         COO.sup.n C.sub.4 H.sub.9                             1-624  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         COO.sup.n C.sub.5 H.sub.11                            1-625  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         COO.sup.i C.sub.3 H.sub.7                             1-626  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         COOCH.sub.2 CH.sub.2 Cl                               1-627  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         COOCH.sub.2 CH.sub.2 Br                               1-628  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         CON(CH.sub.3).sub.2                                   1-629  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         CONHCH.sub.3                                          1-630  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         CON(C.sub.2 H.sub.5).sub.2                            1-631  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         CONHC.sub.2 H.sub.5                                   1-632  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         COCH.sub.3                                            1-633  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         COC.sub.2 H.sub.5                                     1-634  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         COCH.sub.2 Cl                                         1-635  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         CHO                                                   1-636  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         CH═CHCOOCH.sub.3                                  1-637  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         CH═CHCOOC.sub.2 H.sub.5                           1-638  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         CH.sub.2 CH.sub.2 COOCH.sub.3                         1-639  H  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         CH.sub.2 CH.sub.2 COOC.sub.2 H.sub.5                  1-640  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         COOH                                                  1-641  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         COOCH.sub.3                                           1-642  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         COOC.sub.2 H.sub.5                                    1-643  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         COO.sup.n C.sub.3 H.sub.7                             1-644  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         COO.sup.n C.sub.4 H.sub.9                             1-645  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         COO.sup.n C.sub.5 H.sub.11                            1-646  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         COO.sup.i C.sub.3 H.sub.7                             1-647  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         COOCH.sub.2 CH.sub.2 Cl                               1-648  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         COOCH.sub.2 CH.sub.2 Br                               1-649  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         CON(CH.sub.3).sub.2                                   1-650  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         CONHCH.sub.3                                          1-651  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         CON(C.sub.2 H.sub.5).sub.2                            1-652  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         CONHC.sub.2 H.sub.5                                   1-653  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         COCH.sub.3                                            1-654  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         COC.sub.2 H.sub.5                                     1-655  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         COCH.sub.2 Cl                                         1-656  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         CHO                                                   1-657  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         CH═CHCOOCH.sub.3                                  1-658  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         CH═CHCOOC.sub.2 H.sub.5                           1-659  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         CH.sub.2 CH.sub.2 COOCH.sub.3                         1-660  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         CH.sub.2 CH.sub.2 COOC.sub.2 H.sub.5                  1-661  Cl Cl  H  CH.sub.3                                                                          C.sub.2 H.sub.5                                                                  H                                                     1-662  Cl Cl  H  CH.sub.3                                                                          CH.sub.3                                                                         H                                                     1-663  F  F   H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)COOC.sub.2 H.sub.5                      1-664  Cl Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         H                                                     1-665  Cl Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NO.sub.2                                              1-666  Cl Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NH.sub.2                                              1-667  Cl Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)COOC.sub.2 H.sub.5                      1-668  Cl Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHSO.sub.2 CH.sub.3                                   1-669  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCOCH.sub.3                                          1-670  Cl Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OH                                                    1-671  Cl Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3).sub.2                                   1-672  Cl Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 C.tbd.CH                                    1-673  Cl Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)C.tbd.CH                                 1-674  Cl Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COOCH.sub.3                                 1-675  Cl Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COOC.sub.2 H.sub.5                          1-676  Cl Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COOCH.sub.3                              1-677  Cl Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COOC.sub.2 H.sub.5                       1-678  Cl Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 COOCH.sub.3                                 1-679  Cl Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 COOC.sub.2 H.sub.5                          1-680  Cl Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)COOCH.sub.3                              1-681  Cl Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)COOC.sub.2 H.sub.5                       1-682  Cl Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 COOCH.sub.3                                1-683  Cl Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)COOCH.sub.3                             1-684  Cl Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)COOC.sub.2 H.sub.5                      1-685  F  Br  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 C.tbd.CH                                    1-686  F  Br  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COOC.sub.2 H.sub.5                          1-687  F  Br  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COOC.sub.2 H.sub.5                       1-688  F  Br  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 COOC.sub.2 H.sub.5                          1-689  F  Br  H  CF.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)COOC.sub.2 H.sub.5                       1-690  F  Br  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 COOC.sub.2 H.sub.5                         1-691  F  Br  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)COOC.sub.2 H.sub.5                      1-692  F  F   H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 C.tbd.CH                                    1-693  F  F   H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COOC.sub.2 H.sub.5                          1-694  F  F   H  CF.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COOC.sub.2 H.sub.5                       1-695  F  F   H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 COOC.sub.2 H.sub.5                         1-696  F  F   H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)COOC.sub.2 H.sub.5                      1-697  F  F   H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 COOC.sub.2 H.sub.5                          1-698  F  F   H  CF.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)COOC.sub.2 H.sub.5                       1-699  Cl F   H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 C.tbd.CH                                    1-700  Cl F   H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 COOC.sub.2 H.sub.5                          1-701  Cl F   H  CF.sub.3                                                                          CH.sub.3                                                                         OCH(CH.sub.3)COOC.sub.2 H.sub.5                       1-702  Cl F   H  CF.sub.3                                                                          CH.sub.3                                                                         SCH.sub.2 COOC.sub.2 H.sub.5                          1-703  Cl F   H  CF.sub.3                                                                          CH.sub.3                                                                         SCH(CH.sub.3)COOC.sub.2 H.sub.5                       1-704  Cl F   H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 COOC.sub.2 H.sub.5                         1-705  Cl F   H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH(CH.sub.3)COOC.sub.2 H.sub.5                      1-706  F  Cl  H  CF.sub.2 H                                                                        CH.sub.3                                                                         OCH(CH.sub.3).sub.2                                   1-707  F  Cl  H  CF.sub.2 H                                                                        CH.sub.3                                                                         OCH.sub.2 C.tbd.CH                                    1-708  F  Cl  H  CF.sub.2 CF.sub.3                                                                 CH.sub.3                                                                         OCH(CH.sub.3).sub.2                                   1-709  F  Cl  H  CF.sub.2 CF.sub.3                                                                 CH.sub.3                                                                         OCH.sub.2 C.tbd.CH                                    1-710  F  Cl  H  CF.sub.2 Cl                                                                       CH.sub.3                                                                         OCH(CH.sub.3).sub.2                                   1-711  F  Cl  H  CF.sub.2 Cl                                                                       CH.sub.3                                                                         OCH.sub.2 C.tbd.CH                                    1-712  Cl Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         NHCH.sub.2 COOC.sub.2 H.sub.5                         1-713  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         CH.sub.2 CHClCOOC.sub.2 H.sub.5                       1-714  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         I                                                     1-715  F  Cl  H  CF.sub.3                                                                          CH.sub.3                                                                         OCH.sub.2 C(CH.sub.3)═CH.sub.2                    __________________________________________________________________________

                  TABLE 2                                                         ______________________________________                                        Compounds of the formula:                                                      ##STR40##                                                                    Com-                                                                          pound                                                                         No.   X     Z.sup.1                                                                             n   R.sup.1                                                                           R.sup.2                                                                            R.sup.3                                                                            R.sup.4                                                                            R.sup.5                              ______________________________________                                        2-1   H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    H                                    2-2   H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.3                             2-3   H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    C.sub.2 H.sub.5                      2-4   H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    .sup.n C.sub.3 H.sub.7               2-5   H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    .sup.i C.sub.3 H.sub.7               2-6   H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    .sup.i C.sub.4 H.sub.9               2-7   H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    .sup.n C.sub.4 H.sub.9               2-8   H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 CH.sub.2 Cl                 2-9   H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 CH.sub.2 Br                 2-10  H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 CH═CH.sub.2             2-11  H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)CH═CH.sub.2          2-12  H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 CCl═CH.sub.2            2-13  H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 C.tbd.CH                    2-14  H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)C.tbd.CH                 2-15  H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 CN                          2-16  H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OCH.sub.3                   2-17  H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OC.sub.2 H.sub.5            2-18  H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 COOH                        2-19  H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 COOCH.sub.3                 2-20  H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 COOC.sub.2 H.sub.5          2-21  H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 COO.sup.n C.sub.3                                                    H.sub.7                              2-22  H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 COO.sup.n C.sub.4                                                    H.sub.9                              2-23  H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 COO.sup.n C.sub.5                                                    H.sub.11                             2-24  H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 COO.sup.i C.sub.3                                                    H.sub.7                              2-25  H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 COO.sup.c C.sub.5                                                    H.sub.9                              2-26  H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 COO.sup.c C.sub.6                                                    H.sub.11                             2-27  H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)COOH                     2-28  H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)COOCH.sub.3              2-29  H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)COOC.sub.2 H.sub.5       2-30  H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)COO.sup.n C.sub.3                                                 H.sub.7                              2-31  H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)COO.sup.n C.sub.4                                                 H.sub.9                              2-32  H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)COO.sup.n C.sub.5                                                 H.sub.11                             2-33  H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)COO.sup.i C.sub.3                                                 H.sub.7                              2-34  H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)COO.sup.c C.sub.5                                                 H.sub.9                              2-35  H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)COO.sup.c C.sub.6                                                 H.sub.11                             2-36  H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H                                    2-37  H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                             2-38  H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           C.sub.2 H.sub.5                      2-39  H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           .sup.n C.sub.3 H.sub.7               2-40  H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           .sup.i C.sub.3 H.sub.7               2-41  H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           .sup.i C.sub.4 H.sub.9               2-42  H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           .sup.n C.sub.4 H.sub.9               2-43  H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 CH═CH.sub.2             2-44  H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH(CH.sub.3)CH═CH.sub.2          2-45  H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 C.tbd.CH                    2-46  H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH(CH.sub.3)C.tbd.CH                 2-47  H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OCH.sub.3                   2-48  H     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OC.sub.2 H.sub.5            2-49  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    H                                    2-50  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.3                             2-51  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    C.sub.2 H.sub.5                      2-52  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    .sup.n C.sub.3 H.sub.7               2-53  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    .sup.i C.sub.3 H.sub.7               2-54  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    .sup.i C.sub.4 H.sub.9               2-55  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    .sup.n C.sub.4 H.sub.9               2-56  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 CH.sub.2 Cl                 2-57  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 CH.sub.2 Br                 2-58  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 CH═CH.sub.2             2-59  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)CH═CH.sub.2          2-60  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 CCl═CH.sub.2            2-61  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 C.tbd.CH                    2-62  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)C.tbd.CH                 2-63  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 CN                          2-64  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OCH.sub.3                   2-65  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OC.sub.2 H.sub.5            2-66  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 COOH                        2-67  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 COOCH.sub.3                 2-68  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 COOC.sub.2 H.sub.5          2-69  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 COO.sup.n C.sub.3                                                    H.sub.7                              2-70  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 COO.sup.n C.sub.4                                                    H.sub.9                              2-71  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 COO.sup.n C.sub.5                                                    H.sub.11                             2-72  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 COO.sup.i C.sub.3                                                    H.sub.7                              2-73  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 COO.sup.c C.sub.5                                                    H.sub.9                              2-74  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 COO.sup.c C.sub.6                                                    H.sub.11                             2-75  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)COOH                     2-76  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)COOCH.sub.3              2-77  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)COOC.sub.2 H.sub.5       2-78  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)COO.sup.n C.sub.3                                                 H.sub.7                              2-79  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)COO.sup.n C.sub.4                                                 H.sub.9                              2-80  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)COO.sup.n C.sub.5                                                 H.sub.11                             2-81  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)COO.sup.i C.sub.3                                                 H.sub.7                              2-82  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)COO.sup.c C.sub.5                                                 H.sub.9                              2-83  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)COO.sup.c C.sub.6                                                 H.sub.11                             2-84  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H                                    2-85  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                             2-86  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           C.sub.2 H.sub.5                      2-87  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           .sup.n C.sub.3 H.sub.7               2-88  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           .sup.i C.sub.3 H.sub.7               2-89  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           .sup.i C.sub.4 H.sub.9               2-90  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           .sup.n C.sub.4 H.sub.9               2-91  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 CH═CH.sub.2             2-92  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH(CH.sub.3)CH═CH.sub.2          2-93  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 C.tbd.CH                    2-94  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH(CH.sub.3)C.tbd.CH                 2-95  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OCH.sub.3                   2-96  F     O     1   H   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OC.sub.2 H.sub.5            2-97  H     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   H                                    2-98  H     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.3                             2-99  H     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   C.sub.2 H.sub.5                      2-100 H     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   .sup.n C.sub.3 H.sub.7               2-101 H     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   .sup.n C.sub.4 H.sub.9               2-102 H     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   .sup.i C.sub.3 H.sub.7               2-103 H     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   .sup.i C.sub.4 H.sub.9               2-104 H     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 CH.sub.2 Cl                 2-105 H     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 CH.sub.2 Br                 2-106 H     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 CH═CH.sub.2             2-107 H     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)CH═CH.sub.2          2-108 H     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 CCl═CH.sub.2            2-109 H     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 C.tbd.CH                    2-110 H     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)C.tbd.CH                 2-111 H     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 CN                          2-112 H     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 OCH.sub.3                   2-113 H     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 OC.sub.2 H.sub.5            2-114 H     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 COOH                        2-115 H     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 COOCH.sub.3                 2-116 H     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 COOC.sub.2 H.sub.5          2-117 H     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 COO.sup.n C.sub.3                                                    H.sub.7                              2-118 H     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 COO.sup.n C.sub.4                                                    H.sub.9                              2-119 H     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 COO.sup.n C.sub.5                                                    H.sub.11                             2-120 H     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 COO.sup.i C.sub.3                                                    H.sub.7                              2-121 H     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 COO.sup.c C.sub.5                                                    H.sub.9                              2-122 H     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 COO.sup.c C.sub.6                                                    H.sub.11                             2-123 H     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)COOH                     2-124 H     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)COOCH.sub.3              2-125 H     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)COOC.sub.2 H.sub.5       2-126 H     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)COO.sup.n C.sub.3                                                 H.sub.7                              2-127 H     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)COO.sup.n C.sub.4                                                 H.sub.9                              2-128 H     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)COO.sup.n C.sub.5                                                 H.sub.11                             2-129 H     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)COO.sup.i C.sub.3                                                 H.sub.7                              2-130 H     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)COO.sup.c C.sub.5                                                 H.sub.9                              2-131 H     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)COO.sup.c C.sub.6                                                 H.sub.11                             2-132 F     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   H                                    2-133 F     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.3                             2-134 F     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   C.sub.2 H.sub.5                      2-135 F     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   .sup.n C.sub.3 H.sub.7               2-136 F     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   .sup.n C.sub.4 H.sub.9               2-137 F     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   .sup.i C.sub.3 H.sub.7               2-138 F     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   .sup.i C.sub.4 H.sub.9               2-139 F     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 CH.sub.2 Cl                 2-140 F     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 CH.sub.2 Br                 2-141 F     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 CH═CH.sub.2             2-142 F     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)CH═CH.sub.2          2-143 F     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 CCl═CH.sub.2            2-144 F     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 C.tbd.CH                    2-145 F     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)C.tbd.CH                 2-146 F     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 CN                          2-147 F     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 OCH.sub.3                   2-148 F     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 OC.sub.2 H.sub.5            2-149 F     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 COOH                        2-150 F     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 COOCH.sub.3                 2-151 F     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 COOC.sub.2 H.sub.5          2-152 F     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 COO.sup.n C.sub.3                                                    H.sub.7                              2-153 F     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 COO.sup.n C.sub.4                                                    H.sub.9                              2-154 F     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 COO.sup.n C.sub.5                                                    H.sub.11                             2-155 F     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 COO.sup.i C.sub.3                                                    H.sub.7                              2-156 F     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 COO.sup.c C.sub.5                                                    H.sub.9                              2-157 F     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 COO.sup.c C.sub.6                                                    H.sub.11                             2-158 F     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)COOH                     2-159 F     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)COOCH.sub.3              2-160 F     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)COOC.sub.2 H.sub.5       2-161 F     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)COO.sup.n C.sub.3                                                 H.sub.7                              2-162 F     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)COO.sup.n C.sub.4                                                 H.sub.9                              2-163 F     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)COO.sup.n C.sub.5                                                 H.sub.11                             2-164 F     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)COO.sup.i C.sub.3                                                 H.sub.7                              2-165 F     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)COO.sup.c C.sub.5                                                 H.sub.9                              2-166 F     S     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)COO.sup.c C.sub.6                                                 H.sub.11                             2-167 H     O     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   H                                    2-168 H     O     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.3                             2-169 H     O     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   C.sub.2 H.sub.5                      2-170 H     O     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   .sup.n C.sub.3 H.sub.7               2-171 H     O     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   .sup.n C.sub.4 H.sub.9               2-172 H     O     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   .sup.i C.sub.3 H.sub.7               2-173 H     O     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   .sup.i C.sub.4 H.sub.9               2-174 H     O     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 CH═CH.sub.2             2-175 H     O     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)CH═CH.sub.2          2-176 H     O     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 C.tbd.CH                    2-177 H     O     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)C.tbd.CH                 2-178 H     O     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 OCH.sub.3                   2-179 H     O     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 OC.sub.2 H.sub.5            2-180 F     O     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   H                                    2-181 F     O     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.3                             2-182 F     O     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   C.sub.2 H.sub.5                      2-183 F     O     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   .sup.n C.sub.3 H.sub.7               2-184 F     O     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   .sup.n C.sub.4 H.sub.9               2-185 F     O     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 CH═CH.sub.2             2-186 F     O     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)CH═CH.sub.2          2-187 F     O     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 C.tbd.CH                    2-188 F     O     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)C.tbd.CH                 2-189 F     O     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 OCH.sub.3                   2-190 F     O     0   H   CH.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 OC.sub.2 H.sub.5            2-191 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    H                                    2-192 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.3                             2-193 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    C.sub.2 H.sub.5                      2-194 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    .sup.n C.sub.3 H.sub.7               2-195 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    .sup.i C.sub.3 H.sub.7               2-196 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    .sup.i C.sub.4 H.sub.9               2-197 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    .sup.n C.sub.4 H.sub.9               2-198 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 CH.sub.2 Cl                 2-199 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 CH.sub.2 Br                 2-200 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 CH═CH.sub.2             2-201 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)CH═CH.sub.2          2-202 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 CCl═CH.sub.2            2-203 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 C.tbd.CH                    2-204 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)C.tbd.CH                 2-205 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 CN                          2-206 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OCH.sub.3                   2-207 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OC.sub.2 H.sub.5            2-208 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 COOH                        2-209 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 COOCH.sub.3                 2-210 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 COOC.sub.2 H.sub.5          2-211 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 COO.sup.n C.sub.3                                                    H.sub.7                              2-212 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 COO.sup.n C.sub.4                                                    H.sub.9                              2-213 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 COO.sup.n C.sub.5                                                    H.sub.11                             2-214 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 COO.sup.i C.sub.3                                                    H.sub.7                              2-215 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 COO.sup.c C.sub.5                                                    H.sub.9                              2-216 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 COO.sup.c C.sub.6                                                    H.sub.11                             2-217 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)COOH                     2-218 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)COOCH.sub.3              2-219 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)COOC.sub.2 H.sub.5       2-220 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)COO.sup.n C.sub.3                                                 H.sub.7                              2-221 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)COO.sup.n C.sub.4                                                 H.sub.9                              2-222 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)COO.sup.n C.sub.5                                                 H.sub.11                             2-223 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)COO.sup.i C.sub.3                                                 H.sub.7                              2-224 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)COO.sup.c C.sub.5                                                 H.sub.9                              2-225 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)COO.sup.c C.sub.6                                                 H.sub.11                             2-226 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H                                    2-227 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                             2-228 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           C.sub.2 H.sub.5                      2-229 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           .sup.n C.sub.3 H.sub.7               2-230 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           .sup.i C.sub.3 H.sub.7               2-231 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           .sup.i C.sub.4 H.sub.9               2-232 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           .sup.n C.sub.4 H.sub.9               2-233 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 CH═CH.sub.2             2-234 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH(CH.sub.3)CH═CH.sub.2          2-235 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 C.tbd.CH                    2-236 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH(CH.sub.3)C.tbd.CH                 2-237 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OCH.sub.3                   2-238 H     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OC.sub.2 H.sub.5            2-239 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    H                                    2-240 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.3                             2-241 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    C.sub.2 H.sub.5                      2-242 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    .sup.n C.sub.3 H.sub.7               2-243 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    .sup.i C.sub.3 H.sub.7               2-244 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    .sup.i C.sub.4 H.sub.9               2-245 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    .sup.n C.sub.4 H.sub.9               2-246 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 CH.sub.2 Cl                 2-247 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 CH.sub.2 Br                 2-248 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 CH═CH.sub.2             2-249 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)CH═CH.sub.2          2-250 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 CCl═CH.sub.2            2-251 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 C.tbd.CH                    2-252 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)C.tbd.CH                 2-253 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 CN                          2-254 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OCH.sub.3                   2-255 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OC.sub.2 H.sub.5            2-256 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 COOH                        2-257 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 COOCH.sub.3                 2-258 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 COOC.sub.2 H.sub.5          2-259 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 COO.sup.n C.sub.3                                                    H.sub.7                              2-260 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 COO.sup.n C.sub.4                                                    H.sub.9                              2-261 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 COO.sup.n C.sub.5                                                    H.sub.11                             2-262 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 COO.sup.i C.sub.3                                                    H.sub.7                              2-263 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 COO.sup.c C.sub.5                                                    H.sub.9                              2-264 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 COO.sup.c C.sub.6                                                    H.sub.11                             2-265 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)COOH                     2-266 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)COOCH.sub.3              2-267 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)COOC.sub.2 H.sub.5       2-268 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)COO.sup.n C.sub.3                                                 H.sub.7                              2-269 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)COO.sup.n C.sub.4                                                 H.sub.9                              2-270 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)COO.sup.n C.sub.5                                                 H.sub.11                             2-271 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)COO.sup.i C.sub.3                                                 H.sub.7                              2-272 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)COO.sup.c C.sub.5                                                 H.sub.9                              2-273 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           H    CH(CH.sub.3)COO.sup.c C.sub.6                                                 H.sub.11                             2-274 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H                                    2-275 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                             2-276 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           C.sub.2 H.sub.5                      2-277 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           .sup.n C.sub.3 H.sub.7               2-278 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           .sup.i C.sub.3 H.sub.7               2-279 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           .sup.i C.sub.4 H.sub.9               2-280 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           .sup.n C.sub.4 H.sub.9               2-281 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 CH═CH.sub.2             2-282 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH(CH.sub.3)CH═CH.sub.2          2-283 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 C.tbd.CH                    2-284 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH(CH.sub.3)C.tbd.CH                 2-285 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OCH.sub.3                   2-286 F     O     1   H   CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OC.sub.2 H.sub.5            2-287 H     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   H                                    2-288 H     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.3                             2-289 H     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   C.sub.2 H.sub.5                      2-290 H     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   .sup.n C.sub.3 H.sub.7               2-291 H     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   .sup.n C.sub.4 H.sub.9               2-292 H     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   .sup.i C.sub.3 H.sub.7               2-293 H     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   .sup.i C.sub.4 H.sub.9               2-294 H     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 CH.sub.2 Cl                 2-295 H     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 CH.sub.2 Br                 2-296 H     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 CH═CH.sub.2             2-297 H     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)CH═CH.sub.2          2-298 H     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 CCl═CH.sub.2            2-299 H     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 C.tbd.CH                    2-300 H     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)C.tbd.CH                 2-301 H     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 CN                          2-302 H     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 OCH.sub.3                   2-303 H     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 OC.sub.2 H.sub.5            2-304 H     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 COOH                        2-305 H     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 COOCH.sub.3                 2-306 H     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 COOC.sub.2 H.sub.5          2-307 H     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 COO.sup.n C.sub.3                                                    H.sub.7                              2-308 H     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 COO.sup.n C.sub.4                                                    H.sub.9                              2-309 H     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 COO.sup.n C.sub.5                                                    H.sub.11                             2-310 H     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 COO.sup.i C.sub.3                                                    H.sub.7                              2-311 H     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 COO.sup.c C.sub.5                                                    H.sub.9                              2-312 H     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 COO.sup.c C.sub.6                                                    H.sub.11                             2-313 H     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)COOH                     2-314 H     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)COOCH.sub.3              2-315 H     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)COOC.sub.2 H.sub.5       2-316 H     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)COO.sup.n C.sub.3                                                 H.sub.7                              2-317 H     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)COO.sup.n C.sub.4                                                 H.sub.9                              2-318 H     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)COO.sup.n C.sub.5                                                 H.sub.11                             2-319 H     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)COO.sup.i C.sub.3                                                 H.sub.7                              2-320 H     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)COO.sup.c C.sub.5                                                 H.sub.9                              2-321 H     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)COO.sup.c C.sub.6                                                 H.sub.11                             2-322 F     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   H                                    2-323 F     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.3                             2-324 F     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   C.sub.2 H.sub.5                      2-325 F     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   .sup.n C.sub.3 H.sub.7               2-326 F     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   .sup.n C.sub.4 H.sub.9               2-327 F     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   .sup.i C.sub.3 H.sub.7               2-328 F     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   .sup.i C.sub.4 H.sub.9               2-329 F     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 CH.sub.2 Cl                 2-330 F     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 CH.sub.2 Br                 2-331 F     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 CH═CH.sub.2             2-332 F     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)CH═CH.sub.2          2-333 F     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 CCl═CH.sub.2            2-334 F     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 C.tbd.CH                    2-335 F     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)C.tbd.CH                 2-336 F     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 CN                          2-337 F     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 OCH.sub.3                   2-338 F     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 OC.sub.2 H.sub.5            2-339 F     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 COOH                        2-340 F     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 COOCH.sub.3                 2-341 F     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 COOC.sub.2 H.sub.5          2-342 F     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 COO.sup.n C.sub.3                                                    H.sub.7                              2-343 F     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 COO.sup.n C.sub.4                                                    H.sub.9                              2-344 F     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 COO.sup.n C.sub.5                                                    H.sub.11                             2-345 F     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 COO.sup.i C.sub.3                                                    H.sub.7                              2-346 F     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 COO.sup.c C.sub.5                                                    H.sub.9                              2-347 F     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 COO.sup.c C.sub.6                                                    H.sub.11                             2-348 F     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)COOH                     2-349 F     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)COOCH.sub.3              2-350 F     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)COOC.sub.2 H.sub.5       2-351 F     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)COO.sup.n C.sub.3                                                 H.sub.7                              2-352 F     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)COO.sup.n C.sub.4                                                 H.sub.9                              2-353 F     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)COO.sup.n C.sub.5                                                 H.sub.11                             2-354 F     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)COO.sup.i C.sub.3                                                 H.sub.7                              2-355 F     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)COO.sup.c C.sub.5                                                 H.sub.9                              2-356 F     S     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)COO.sup.c C.sub.6                                                 H.sub.11                             2-357 H     O     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   H                                    2-358 H     O     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.3                             2-359 H     O     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   C.sub.2 H.sub.5                      2-360 H     O     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   .sup.n C.sub.3 H.sub.7               2-361 H     O     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   .sup.n C.sub.4 H.sub.9               2-362 H     O     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   .sup.i C.sub.3 H.sub.7               2-363 H     O     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   .sup.i C.sub.4 H.sub.9               2-364 H     O     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 CH═CH.sub.2             2-365 H     O     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)CH═CH.sub.2          2-366 H     O     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 C.tbd.CH                    2-367 H     O     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)C.tbd.CH                 2-368 H     O     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 OCH.sub.3                   2-369 H     O     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 OC.sub.2 H.sub.5            2-370 F     O     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   H                                    2-371 F     O     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.3                             2-372 F     O     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   C.sub.2 H.sub.5                      2-373 F     O     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   .sup.n C.sub.3 H.sub.7               2-374 F     O     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   .sup.n C.sub.4 H.sub.9               2-375 F     O     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 CH═CH.sub.2             2-376 F     O     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)CH═CH.sub.2          2-377 F     O     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 C.tbd.CH                    2-378 F     O     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH(CH.sub.3)C.tbd.CH                 2-379 F     O     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 OCH.sub.3                   2-380 F     O     0   H   CF.sub.3                                                                           CH.sub.3                                                                           --   CH.sub.2 OC.sub.2 H.sub.5            ______________________________________                                    

                  TABLE 3                                                         ______________________________________                                        Compounds of the formula:                                                      ##STR41##                                                                    Compound                                                                      No.     X     Y      Z.sup.2                                                                           R.sup.1                                                                            R.sup.2                                                                            R.sup.3                                                                             R.sup.6                              ______________________________________                                        3-1     H     F      O   H    CH.sub.3                                                                           C.sub.2 H.sub.5                                                                     CH.sub.3                             3-2     H     Cl     O   H    CH.sub.3                                                                           C.sub.2 H.sub.5                                                                     CH.sub.3                             3-3     H     Br     O   H    CH.sub.3                                                                           C.sub.2 H.sub.5                                                                     CH.sub.3                             3-4     F     F      O   H    CH.sub.3                                                                           C.sub.2 H.sub.5                                                                     CH.sub.3                             3-5     F     Cl     O   H    CH.sub.3                                                                           C.sub.2 H.sub.5                                                                     CH.sub.3                             3-6     F     Br     O   H    CH.sub.3                                                                           C.sub.2 H.sub.5                                                                     CH.sub.3                             3-7     H     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                             3-8     H     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                             3-9     H     Br     O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                             3-10    F     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                             3-11    F     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                             3-12    F     Br     O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                             3-13    H     F      O   H    CH.sub.3                                                                           C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                      3-14    H     Cl     O   H    CH.sub.3                                                                           C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                      3-15    H     Br     O   H    CH.sub.3                                                                           C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                      3-16    F     F      O   H    CH.sub.3                                                                           C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                      3-17    F     Cl     O   H    CH.sub.3                                                                           C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                      3-18    F     Br     O   H    CH.sub.3                                                                           C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                      3-19    H     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            C.sub.2 H.sub.5                      3-20    H     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            C.sub.2 H.sub.5                      3-21    H     Br     O   H    CH.sub.3                                                                           CH.sub.3                                                                            C.sub.2 H.sub.5                      3-22    F     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            C.sub.2 H.sub.5                      3-23    F     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            C.sub.2 H.sub.5                      3-24    F     Br     O   H    CH.sub.3                                                                           CH.sub.3                                                                            C.sub.2 H.sub.5                      3-25    H     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 Br                          3-26    H     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            CHBr.sub.2                           3-27    H     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            CBr.sub.3                            3-28    H     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            CHO                                  3-29    H     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            CN                                   3-30    H     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            COOH                                 3-31    H     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OH                          3-32    H     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCH.sub.3                   3-33    H     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OC.sub.2 H.sub.5            3-34    H     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 O.sup.i C.sub.3                                                      H.sub.7                              3-35    H     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCH.sub.2 OCH.sub.3         3-36    H     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCH.sub.2 OC.sub.2                                                   H.sub.5                              3-37    H     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCOCH.sub.3                 3-38    H     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCOC.sub.2 H.sub.5          3-39    H     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCO.sup.i C.sub.3                                                    H.sub.7                              3-40    H     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCOCH.sub.2 Cl              3-41    H     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCOCCl.sub.3                3-42    H     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCOCF.sub.3                 3-43    H     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            COOCH.sub.3                          3-44    H     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            COOC.sub.2 H.sub.5                   3-45    H     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            COO.sup.n C.sub.3 H.sub.7            3-46    H     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            COO.sup.n C.sub.4 H.sub.9            3-47    H     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            COO.sup.n C.sub.5 H.sub.11           3-48    H     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            COO.sup.i C.sub.3 H.sub.7            3-49    H     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            COCH.sub.3                           3-50    H     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            COC.sub.2 H.sub.5                    3-51    H     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 Br                          3-52    H     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            CHBr.sub.2                           3-53    H     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            CBr.sub.3                            3-54    H     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            CHO                                  3-55    H     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            CN                                   3-56    H     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            COOH                                 3-57    H     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OH                          3-58    H     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCH.sub.3                   3-59    H     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OC.sub.2 H.sub.5            3-60    H     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 O.sup.i C.sub.3                                                      H.sub.7                              3-61    H     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCH.sub.2 OCH.sub.3         3-62    H     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCH.sub.2 OC.sub.2                                                   H.sub.5                              3-63    H     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCOCH.sub.3                 3-64    H     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCOC.sub.2 H.sub.5          3-65    H     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCO.sup.i C.sub.3                                                    H.sub.7                              3-66    H     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCOCH.sub.2 Cl              3-67    H     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCOCCl.sub.3                3-68    H     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCOCF.sub.3                 3-69    H     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            COOCH.sub.3                          3-70    H     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            COOC.sub.2 H.sub.5                   3-71    H     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            COO.sup.n C.sub.3 H.sub.7            3-72    H     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            COO.sup.n C.sub.4 H.sub.9            3-73    H     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            COO.sup.n C.sub.5 H.sub.11           3-74    H     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            COO.sup.i C.sub.3 H.sub.7            3-75    H     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            COCH.sub.3                           3-76    H     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            COC.sub.2 H.sub.5                    3-77    F     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 Br                          3-78    F     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            CHBr.sub.2                           3-79    F     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            CBr.sub.3                            3-80    F     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            CHO                                  3-81    F     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            CN                                   3-82    F     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            COOH                                 3-83    F     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OH                          3-84    F     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCH.sub.3                   3-85    F     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OC.sub.2 H.sub.5            3-86    F     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 O.sup.i C.sub.3                                                      H.sub.7                              3-87    F     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCH.sub.2 OCH.sub.3         3-88    F     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCH.sub.2 OC.sub.2                                                   H.sub.5                              3-89    F     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCOCH.sub.3                 3-90    F     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCOC.sub.2 H.sub.5          3-91    F     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCO.sup.i C.sub.3                                                    H.sub.7                              3-92    F     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCOCH.sub.2 Cl              3-93    F     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCOCCl.sub.3                3-94    F     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCOCF.sub.3                 3-95    F     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            COOCH.sub.3                          3-96    F     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            COOC.sub.2 H.sub.5                   3-97    F     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            COO.sup.n C.sub.3 H.sub.7            3-98    F     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            COO.sup.n C.sub.4 H.sub.9            3-99    F     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            COO.sup.n C.sub.5 H.sub.11           3-100   F     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            COO.sup.i C.sub.3 H.sub.7            3-101   F     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            COCH.sub.3                           3-102   F     F      O   H    CH.sub.3                                                                           CH.sub.3                                                                            COC.sub.2 H.sub.5                    3-103   F     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 Br                          3-104   F     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            CHBr.sub.2                           3-105   F     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            CBr.sub.3                            3-106   F     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            CHO                                  3-107   F     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            CN                                   3-108   F     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            COOH                                 3-109   F     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OH                          3-110   F     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCH.sub.3                   3-111   F     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OC.sub.2 H.sub.5            3-112   F     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 O.sup.i C.sub.3                                                      H.sub.7                              3-113   F     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCH.sub.2 OCH.sub.3         3-114   F     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCH.sub.2 OC.sub.2                                                   H.sub.5                              3-115   F     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCOCH.sub.3                 3-116   F     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCOC.sub.2 H.sub.5          3-117   F     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCO.sup.i C.sub.3                                                    H.sub.7                              3-118   F     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCOCH.sub.2 Cl              3-119   F     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCOCCl.sub.3                3-120   F     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCOCF.sub.3                 3-121   F     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            COOCH.sub.3                          3-122   F     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            COOC.sub.2 H.sub.5                   3-123   F     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            COO.sup.n C.sub.3 H.sub.7            3-124   F     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            COO.sup.n C.sub.4 H.sub.9            3-125   F     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            COO.sup.n C.sub.5 H.sub.11           3-126   F     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            COO.sup.i C.sub.3 H.sub.7            3-127   F     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            COCH.sub.3                           3-128   F     Cl     O   H    CH.sub.3                                                                           CH.sub.3                                                                            COC.sub.2 H.sub.5                    3-129   H     F      O   H    CF.sub.3                                                                           C.sub.2 H.sub.5                                                                     CH.sub.3                             3-130   H     Cl     O   H    CF.sub.3                                                                           C2 H.sub.5                                                                          CH.sub.3                             3-131   H     Br     O   H    CF.sub.3                                                                           C.sub.2 H.sub.5                                                                     CH.sub.3                             3-132   F     F      O   H    CF.sub.3                                                                           C.sub.2 H.sub.5                                                                     CH.sub.3                             3-133   F     Cl     O   H    CF.sub.3                                                                           C.sub.2 H.sub.5                                                                     CH.sub.3                             3-134   F     Br     O   H    CF.sub.3                                                                           C.sub.2 H.sub.5                                                                     CH.sub.3                             3-135   H     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                             3-136   H     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                             3-137   H     Br     O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                             3-138   F     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                             3-139   F     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                             3-140   F     Br     O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                             3-141   H     F      O   H    CF.sub.3                                                                           C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                      3-142   H     Cl     O   H    CF.sub.3                                                                           C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                      3-143   H     Br     O   H    CF.sub.3                                                                           C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                      3-144   F     F      O   H    CF.sub.3                                                                           C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                      3-145   F     Cl     O   H    CF.sub.3                                                                           C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                      3-146   F     Br     O   H    CF.sub.3                                                                           C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                      3-147   H     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            C.sub.2 H.sub.5                      3-148   H     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            C.sub.2 H.sub.5                      3-149   H     Br     O   H    CF.sub.3                                                                           CH.sub.3                                                                            C.sub.2 H.sub.5                      3-150   F     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            C.sub.2 H.sub.5                      3-151   F     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            C.sub.2 H.sub.5                      3-152   F     Br     O   H    CF.sub.3                                                                           CH.sub.3                                                                            C.sub.2 H.sub.5                      3-153   H     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 Br                          3-154   H     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            CHBr.sub.2                           3-155   H     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            CBr.sub.3                            3-156   H     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            CHO                                  3-157   H     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            CN                                   3-158   H     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            COOH                                 3-159   H     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OH                          3-160   H     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCH.sub.3                   3-161   H     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OC.sub.2 H.sub.5            3-162   H     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 O.sup.i C.sub.3                                                      H.sub.7                              3-163   H     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCH.sub.2 OCH.sub.3         3-164   H     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCH.sub.2 OC.sub.2                                                   H.sub.5                              3-165   H     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCOCH.sub.3                 3-166   H     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCOC.sub.2 H.sub.5          3-167   H     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCO.sup.i C.sub.3                                                    H.sub.7                              3-168   H     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCOCH.sub.2 Cl              3-169   H     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCOCCl.sub.3                3-170   H     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCOCF.sub.3                 3-171   H     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            COOCH.sub.3                          3-172   H     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            COOC.sub.2 H.sub.5                   3-173   H     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            COO.sup.n C.sub.3 H.sub.7            3-174   H     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            COO.sup.n C.sub.4 H.sub.9            3-175   H     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            COO.sup.n C.sub.5 H.sub.11           3-176   H     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            COO.sup.i C.sub.3 H.sub.7            3-177   H     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            COCH.sub.3                           3-178   H     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            COC.sub.2 H.sub.5                    3-179   H     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 Br                          3-180   H     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            CHBr.sub.2                           3-181   H     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            CBr.sub.3                            3-182   H     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            CHO                                  3-183   H     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            CN                                   3-184   H     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            COOH                                 3-185   H     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OH                          3-186   H     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCH.sub.3                   3-187   H     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OC.sub.2 H.sub.5            3-188   H     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 O.sup.i C.sub.3                                                      H.sub.7                              3-189   H     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCH.sub.2 OCH.sub.3         3-190   H     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCH.sub.2 OC.sub.2                                                   H.sub.5                              3-191   H     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCOCH.sub.3                 3-192   H     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCOC.sub.2 H.sub.5          3-193   H     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCO.sup.i C.sub.3                                                    H.sub.7                              3-194   H     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCOCH.sub.2 Cl              3-195   H     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCOCCl.sub.3                3-196   H     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCOCF.sub.3                 3-197   H     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            COOCH.sub.3                          3-198   H     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            COOC.sub.2 H.sub.5                   3-199   H     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            COO.sup.n C.sub.3 H.sub.7            3-200   H     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            COO.sup.n C.sub.4 H.sub.9            3-201   H     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            COO.sup.n C.sub.5 H.sub.11           3-202   H     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            COO.sup.i C.sub.3 H.sub.7            3-203   H     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            COCH.sub.3                           3-204   H     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            COC.sub.2 H.sub.5                    3-205   F     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 Br                          3-206   F     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            CHBr.sub.2                           3-207   F     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            CBr.sub.3                            3-208   F     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            CHO                                  3-209   F     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            CN                                   3-210   F     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            COOH                                 3-211   F     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OH                          3-212   F     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCH.sub.3                   3-213   F     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OC.sub.2 H.sub.5            3-214   F     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 O.sup.i C.sub.3                                                      H.sub.7                              3-215   F     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCH.sub.2 OCH.sub.3         3-216   F     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCH.sub.2 OC.sub.2                                                   H.sub.5                              3-217   F     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCOCH.sub.3                 3-218   F     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCOC.sub.2 H.sub.5          3-219   F     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCO.sup.i C.sub.3                                                    H.sub.7                              3-220   F     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCOCH.sub.2 Cl              3-221   F     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCOCCl.sub.3                3-222   F     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCOCF.sub.3                 3-223   F     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            COOCH.sub.3                          3-224   F     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            COOC.sub.2 H.sub.5                   3-225   F     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            COO.sup.n C.sub.3 H.sub.7            3-226   F     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            COO.sup.n C.sub.4 H.sub.9            3-227   F     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            COO.sup.n C.sub.5 H.sub.11           3-228   F     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            COO.sup.i C.sub.3 H.sub.7            3-229   F     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            COCH.sub.3                           3-230   F     F      O   H    CF.sub.3                                                                           CH.sub.3                                                                            COC.sub.2 H.sub.5                    3-231   F     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 Br                          3-232   F     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            CHBr.sub.2                           3-233   F     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            CBr.sub.3                            3-234   F     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            CHO                                  3-235   F     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            CN                                   3-236   F     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            COOH                                 3-237   F     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OH                          3-238   F     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCH.sub.3                   3-239   F     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OC.sub.2 H.sub.5            3-240   F     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 O.sup.i C.sub.3                                                      H.sub.7                              3-241   F     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCH.sub.2 OCH.sub.3         3-242   F     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCH.sub.2 OC.sub.2                                                   H.sub.5                              3-243   F     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCOCH.sub.3                 3-244   F     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCOC.sub.2 H.sub.5          3-245   F     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCO.sup.i C.sub.3                                                    H.sub.7                              3-246   F     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCOCH.sub.2 Cl              3-247   F     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCOCCl.sub.3                3-248   F     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            CH.sub.2 OCOCF.sub.3                 3-249   F     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            COOCH.sub.3                          3-250   F     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            COOC.sub.2 H.sub.5                   3-251   F     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            COO.sup.n C.sub.3 H.sub.7            3-252   F     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            COO.sup.n C.sub.4 H.sub.9            3-253   F     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            COO.sup.n C.sub.5 H.sub.11           3-254   F     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            COO.sup.i C.sub.3 H.sub.7            3-255   F     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            COCH.sub.3                           3-256   F     Cl     O   H    CF.sub.3                                                                           CH.sub.3                                                                            COC.sub.2 H.sub.5                    ______________________________________                                    

                  TABLE 4                                                         ______________________________________                                        Compounds of the formula:                                                      ##STR42##                                                                    Compound                                                                      No.     X     Y     R.sup.1                                                                            R.sup.2                                                                            R.sup.3                                                                            R.sup.7                                                                            R.sup.8                               ______________________________________                                        4-1     H     F     H    CH.sub.3                                                                           C.sub.2 H.sub.5                                                                    H    CH.sub.3                              4-2     H     Cl    H    CH.sub.3                                                                           C.sub.2 H.sub.5                                                                    H    CH.sub.3                              4-3     H     Br    H    CH.sub.3                                                                           C.sub.2 H.sub.5                                                                    H    CH.sub.3                              4-4     H     F     H    CH.sub.3                                                                           C.sub.2 H.sub.5                                                                    H    CH.sub.2 OH                           4-5     H     Cl    H    CH.sub.3                                                                           C.sub.2 H.sub.5                                                                    H    CH.sub.2 OH                           4-6     H     Br    H    CH.sub.3                                                                           C.sub.2 H.sub.5                                                                    H    CH.sub.2 OH                           4-7     H     F     H    CH.sub.3                                                                           C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           CH.sub.3                              4-8     H     Cl    H    CH.sub.3                                                                           C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           CH.sub.3                              4-9     H     Br    H    CH.sub.3                                                                           C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           CH.sub.3                              4-10    H     F     H    CH.sub.3                                                                           C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           CH.sub.2 OH                           4-11    H     Cl    H    CH.sub.3                                                                           C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           CH.sub.2 OH                           4-12    H     Br    H    CH.sub.3                                                                           C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           CH.sub.2 OH                           4-13    F     F     H    CH.sub.3                                                                           C.sub.2 H.sub.5                                                                    H    CH.sub.3                              4-14    F     Cl    H    CH.sub.3                                                                           C.sub.2 H.sub.5                                                                    H    CH.sub.3                              4-15    F     Br    H    CH.sub.3                                                                           C.sub.2 H.sub.5                                                                    H    CH.sub.3                              4-16    F     F     H    CH.sub.3                                                                           C.sub.2 H.sub.5                                                                    H    CH.sub.2 OH                           4-17    F     Cl    H    CH.sub.3                                                                           C.sub.2 H.sub.5                                                                    H    CH.sub.2 OH                           4-18    F     Br    H    CH.sub.3                                                                           C.sub.2 H.sub.5                                                                    H    CH.sub.2 OH                           4-19    F     F     H    CH.sub.3                                                                           C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           CH.sub.3                              4-20    F     Cl    H    CH.sub.3                                                                           C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           CH.sub.3                              4-21    F     Br    H    CH.sub.3                                                                           C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           CH.sub.3                              4-22    F     F     H    CH.sub.3                                                                           C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           CH.sub.2 OH                           4-23    F     Cl    H    CH.sub.3                                                                           C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           CH.sub.2 OH                           4-24    F     Br    H    CH.sub.3                                                                           C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           CH.sub.2 OH                           4-25    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 Cl                           4-26    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 Br                           4-27    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OCH.sub.3                    4-28    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OC.sub.2 H.sub.5             4-29    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OCH.sub.2 OCH.sub.3          4-30    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OCH.sub.2 OC.sub.2                                                   H.sub.5                               4-31    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OCOCH.sub.3                  4-32    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OCOC.sub.2 H.sub.5           4-33    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OCO.sup.i C.sub.3                                                    H.sub.7                               4-34    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OCOCH.sub.2 Cl               4-35    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OCOCCl.sub.3                 4-36    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OCOCF.sub.3                  4-37    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    COOH                                  4-38    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    COOCH.sub.3                           4-39    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    COOC.sub.2 H.sub.5                    4-40    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    COO.sup.n C.sub.3 H.sub.7             4-41    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    COO.sup.n C.sub.4 H.sub.9             4-42    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    COO.sup.n C.sub.5 H.sub.11            4-43    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    COO.sup.i C.sub.3 H.sub.7             4-44    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    COO.sup.c C.sub.5 H.sub.9             4-45    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    COO.sup.c C.sub.6 H.sub.11            4-46    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    COOCH.sub.2 CH═CH.sub.2           4-47    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    COOCH.sub.2 C.tbd.CH                  4-48    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    CONH.sub.2                            4-49    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    CONHCH.sub.3                          4-50    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    CONHC.sub.2 H.sub.5                   4-51    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    CON(CH.sub.3).sub.2                   4-52    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    CON(C.sub.2 H.sub.5).sub.2            4-53    F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 Cl                           4-54    F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 Br                           4-55    F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OCH.sub.3                    4-56    F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OC.sub.2 H.sub.5             4-57    F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OCH.sub.2 OCH.sub.3          4-58    F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OCH.sub.2 OC.sub.2                                                   H.sub.5                               4-59    F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OCOCH.sub.3                  4-60    F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OCOC.sub.2 H.sub.5           4-61    F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OCO.sup.i C.sub.3                                                    H.sub.7                               4-62    F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OCOCH.sub.2 Cl               4-63    F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OCOCCl.sub.3                 4-64    F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OCOCF.sub.3                  4-65    F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    COOH                                  4-66    F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    COOCH.sub.3                           4-67    F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    COOC.sub.2 H.sub.5                    4-68    F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    COO.sup.n C.sub.3 H.sub.7             4-69    F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    COO.sup.n C.sub.4 H.sub.9             4-70    F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    COO.sup.n C.sub.5 H.sub.11            4-71    F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    COO.sup.i C.sub.3 H.sub.7             4-72    F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    COO.sup.c C.sub.5 H.sub.9             4-73    F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    COO.sup.c C.sub.6 H.sub.11            4-74    F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    COOCH.sub.2 CH═CH.sub.2           4-75    F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    COOCH.sub.2 C.tbd.CH                  4-76    F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    CONH.sub.2                            4-77    F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    CONHCH.sub.3                          4-78    F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    CONHC.sub.2 H.sub.5                   4-79    F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    CON(CH.sub.3).sub.2                   4-80    F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           H    CON(C.sub.2 H.sub.5).sub.2            4-81    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 Cl                           4-82    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 Br                           4-83    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OCH.sub.3                    4-84    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OC.sub.2 H.sub.5             4-85    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OCH.sub.2 OCH.sub.3          4-86    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OCH.sub.2 OC.sub.2                                                   H.sub.5                               4-87    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OCOCH.sub.3                  4-88    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OCOC.sub.2 H.sub.5           4-89    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OCO.sup.i C.sub.3                                                    H.sub.7                               4-90    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OCOCH.sub.2 Cl               4-91    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OCOCCl.sub.3                 4-92    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OCOCF.sub.3                  4-93    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COOH                                  4-94    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COOCH.sub.3                           4-95    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COOC.sub.2 H.sub.5                    4-96    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COO.sup.n C.sub.3 H.sub.7             4-97    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COO.sup.n C.sub.4 H.sub.9             4-98    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COO.sup.n C.sub.5 H.sub.11            4-99    H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COO.sup.i C.sub.3 H.sub.7             4-100   H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COO.sup.c C.sub.5 H.sub.9             4-101   H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COO.sup.c C.sub.6 H.sub.11            4-102   H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COOCH.sub.2 CH═CH.sub.2           4-103   H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COOCH.sub.2 C.tbd.CH                  4-104   H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CONH.sub.2                            4-105   H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CONHCH.sub.3                          4-106   H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CONHC.sub.2 H.sub.5                   4-107   H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CON(CH.sub.3).sub.2                   4-108   H     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CON(C.sub.2 H.sub.5).sub.2            4-109   F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 Cl                           4-110   F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 Br                           4-111   F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OCH.sub.3                    4-112   F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OC.sub.2 H.sub.5             4-113   F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OCH.sub.2 OCH.sub.3          4-114   F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OCH.sub.2 OC.sub.2                                                   H.sub.5                               4-115   F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OCOCH.sub.3                  4-116   F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OCOC.sub.2 H.sub.5           4-117   F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OCO.sup.i C.sub.3                                                    H.sub.7                               4-118   F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OCOCH.sub.2 Cl               4-119   F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OCOCCl.sub.3                 4-120   F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OCOCF.sub.3                  4-121   F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COOH                                  4-122   F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COOCH.sub.3                           4-123   F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COOC.sub.2 H.sub.5                    4-124   F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COO.sup.n C.sub.3 H.sub.7             4-125   F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COO.sup.n C.sub.4 H.sub.9             4-126   F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COO.sup.n C.sub.5 H.sub.11            4-127   F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COO.sup.i C.sub.3 H.sub.7             4-128   F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COO.sup.c C.sub.5 H.sub.9             4-129   F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COO.sup.c C.sub.6 H.sub.11            4-130   F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COOCH.sub.2 CH═CH.sub.2           4-131   F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COOCH.sub.2 C.tbd.CH                  4-132   F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CONH.sub.2                            4-133   F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CONHCH.sub.3                          4-134   F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CONHC.sub.2 H.sub.5                   4-135   F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CON(CH.sub.3).sub.2                   4-136   F     Cl    H    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CON(C.sub.2 H.sub.5).sub.2            4-137   H     F     H    CF.sub.3                                                                           C.sub.2 H.sub.5                                                                    H    CH.sub.3                              4-138   H     Cl    H    CF.sub.3                                                                           C.sub.2 H.sub.5                                                                    H    CH.sub.3                              4-139   H     Br    H    CF.sub.3                                                                           C.sub.2 H.sub.5                                                                    H    CH.sub.3                              4-140   H     F     H    CF.sub.3                                                                           C.sub.2 H.sub.5                                                                    H    CH.sub.2 OH                           4-141   H     Cl    H    CF.sub.3                                                                           C.sub.2 H.sub.5                                                                    H    CH.sub.2 OH                           4-142   H     Br    H    CF.sub.3                                                                           C.sub.2 H.sub.5                                                                    H    CH.sub.2 OH                           4-143   H     F     H    CF.sub.3                                                                           C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           CH.sub.3                              4-144   H     Cl    H    CF.sub.3                                                                           C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           CH.sub.3                              4-145   H     Br    H    CF.sub.3                                                                           C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           CH.sub.3                              4-146   H     F     H    CF.sub.3                                                                           C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           CH.sub.2 OH                           4-147   H     Cl    H    CF.sub.3                                                                           C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           CH.sub.2 OH                           4-148   H     Br    H    CF.sub.3                                                                           C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           CH.sub.2 OH                           4-149   F     F     H    CF.sub.3                                                                           C.sub.2 H.sub.5                                                                    H    CH.sub.3                              4-150   F     Cl    H    CF.sub.3                                                                           C.sub.2 H.sub.5                                                                    H    CH.sub.3                              4-151   F     Br    H    CF.sub.3                                                                           C.sub.2 H.sub.5                                                                    H    CH.sub.3                              4-152   F     F     H    CF.sub.3                                                                           C.sub.2 H.sub.5                                                                    H    CH.sub.2 OH                           4-153   F     Cl    H    CF.sub.3                                                                           C.sub.2 H.sub.5                                                                    H    CH.sub.2 OH                           4-154   F     Br    H    CF.sub.3                                                                           C.sub.2 H.sub.5                                                                    H    CH.sub.2 OH                           4-155   F     F     H    CF.sub.3                                                                           C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           CH.sub.3                              4-156   F     Cl    H    CF.sub.3                                                                           C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           CH.sub.3                              4-157   F     Br    H    CF.sub.3                                                                           C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           CH.sub.3                              4-158   F     F     H    CF.sub.3                                                                           C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           CH.sub.2 OH                           4-159   F     Cl    H    CF.sub.3                                                                           C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           CH.sub.2 OH                           4-160   F     Br    H    CF.sub.3                                                                           C.sub.2 H.sub.5                                                                    CH.sub.3                                                                           CH.sub.2 OH                           4-161   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 Cl                           4-162   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 Br                           4-163   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OCH.sub.3                    4-164   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OC.sub.2 H.sub.5             4-165   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OCH.sub.2 OCH.sub.3          4-166   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OCH.sub.2 OC.sub.2                                                   H.sub.5                               4-167   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OCOCH.sub.3                  4-168   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OCOC.sub.2 H.sub.5           4-169   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OCO.sup.i C.sub.3                                                    H.sub.7                               4-170   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OCOCH.sub.2 Cl               4-171   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OCOCCl.sub.3                 4-172   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OCOCF.sub.3                  4-173   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    COOH                                  4-174   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    COOCH.sub.3                           4-175   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    COOC.sub.2 H.sub.5                    4-176   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    COO.sup.n C.sub.3 H.sub.7             4-177   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    COO.sup.n C.sub.4 H.sub.9             4-178   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    COO.sup.n C.sub.5 H.sub.11            4-179   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    COO.sup.i C.sub.3 H.sub.7             4-180   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    COO.sup.c C.sub.5 H.sub.9             4-181   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    COO.sup.c C.sub.6 H.sub.11            4-182   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    COOCH.sub.2 CH═CH.sub.2           4-183   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    COOCH.sub.2 C.tbd.CH                  4-184   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    CONH.sub.2                            4-185   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    CONHCH.sub.3                          4-186   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    CONHC.sub.2 H.sub.5                   4-187   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    CON(CH.sub.3).sub.2                   4-188   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    CON(C.sub.2 H.sub.5).sub.2            4-189   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 Cl                           4-190   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 Br                           4-191   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OCH.sub.3                    4-192   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OC.sub.2 H.sub.5             4-193   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OCH.sub.2 OCH.sub.3          4-194   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OCH.sub.2 OC.sub.2                                                   H.sub.5                               4-195   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OCOCH.sub.3                  4-196   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OCOC.sub.2 H.sub.5           4-197   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OCO.sup.i C.sub.3                                                    H.sub.7                               4-198   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OCOCH.sub.2 Cl               4-199   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OCOCCl.sub.3                 4-200   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.2 OCOCF.sub.3                  4-201   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    COOH                                  4-202   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    COOCH.sub.3                           4-203   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    COOC.sub.2 H.sub.5                    4-204   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    COO.sup.n C.sub.3 H.sub.7             4-205   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    COO.sup.n C.sub.4 H.sub.9             4-206   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    COO.sup.n C.sub.5 H.sub.11            4-207   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    COO.sup.i C.sub.3 H.sub.7             4-208   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    COO.sup.c C.sub.5 H.sub.9             4-209   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    COO.sup.c C.sub.6 H.sub.11            4-210   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    COOCH.sub.2 CH═CH.sub.2           4-211   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    COOCH.sub.2 C.tbd.CH                  4-212   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    CONH.sub.2                            4-213   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    CONHCH.sub.3                          4-214   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    CONHC.sub.2 H.sub.5                   4-215   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    CON(CH.sub.3).sub.2                   4-216   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           H    CON(C.sub.2 H.sub.5).sub.2            4-217   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 Cl                           4-218   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 Br                           4-219   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OCH.sub.3                    4-220   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OC.sub.2 H.sub.5             4-221   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OCH.sub.2 OCH.sub.3          4-222   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OCH.sub.2 OC.sub.2                                                   H.sub.5                               4-223   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OCOCH.sub.3                  4-224   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OCOC.sub.2 H.sub.5           4-225   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OCO.sup.i C.sub.3                                                    H.sub.7                               4-226   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OCOCH.sub.2 Cl               4-227   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OCOCCl.sub.3                 4-228   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OCOCF.sub.3                  4-229   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COOH                                  4-230   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COOCH.sub.3                           4-231   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COOC.sub.2 H.sub.5                    4-232   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COO.sup.n C.sub.3 H.sub.7             4-233   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COO.sup.n C.sub.4 H.sub.9             4-234   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COO.sup.n C.sub.5 H.sub.11            4-235   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COO.sup.i C.sub.3 H.sub.7             4-236   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COO.sup.c C.sub.5 H.sub.9             4-237   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COO.sup.c C.sub.6 H.sub.11            4-238   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COOCH.sub.2 CH═CH.sub.2           4-239   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COOCH.sub.2 C.tbd.CH                  4-240   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CONH.sub.2                            4-241   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CONHCH.sub.3                          4-242   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CONHC.sub.2 H.sub.5                   4-243   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CON(CH.sub.3).sub.2                   4-244   H     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CON(C.sub.2 H.sub.5).sub.2            4-245   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 Cl                           4-246   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 Br                           4-247   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OCH.sub.3                    4-248   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OC.sub.2 H.sub.5             4-249   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OCH.sub.2 OCH.sub.3          4-250   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OCH.sub.2 OC.sub.2                                                   H.sub.5                               4-251   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OCOCH.sub.3                  4-252   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OCOC.sub.2 H.sub.5           4-253   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OCO.sup.i C.sub.3                                                    H.sub.7                               4-254   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OCOCH.sub.2 Cl               4-255   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OCOCCl.sub.3                 4-256   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.2 OCOCF.sub.3                  4-257   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COOH                                  4-258   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COOCH.sub.3                           4-259   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COOC.sub.2 H.sub.5                    4-260   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COO.sup.n C.sub.3 H.sub.7             4-261   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COO.sup.n C.sub.4 H.sub.9             4-262   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COO.sup.n C.sub.5 H.sub.11            4-263   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COO.sup.i C.sub.3 H.sub.7             4-264   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COO.sup.c C.sub.5 H.sub.9             4-265   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COO.sup.c C.sub.6 H.sub.11            4-266   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COOCH.sub.2 CH═CH.sub.2           4-267   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           COOCH.sub.2 C.tbd.CH                  4-268   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CONH.sub.2                            4-269   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CONHCH.sub.3                          4-270   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CONHC.sub.2 H.sub.5                   4-271   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CON(CH.sub.3).sub.2                   4-272   F     Cl    H    CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CON(C.sub.2 H.sub.5).sub.2            ______________________________________                                    

                  TABLE 5                                                         ______________________________________                                        Compounds of the formula:                                                      ##STR43##                                                                    Compound                                                                      No.     X       R.sup.1                                                                              R.sup.2                                                                             R.sup.3                                                                             R.sup.5                                    ______________________________________                                        5-1     H       H      CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                   5-2     H       H      CH.sub.3                                                                            CH.sub.3                                                                            C.sub.2 H.sub.5                            5-3     H       H      CH.sub.3                                                                            CH.sub.3                                                                            .sup.i C.sub.3 H.sub.7                     5-4     H       H      CH.sub.3                                                                            CH.sub.3                                                                            .sup.n C.sub.3 H.sub.7                     5-5     H       H      CH.sub.3                                                                            CH.sub.3                                                                            .sup.i C.sub.4 H.sub.9                     5-6     H       H      CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.2 CH═CH.sub.2                   5-7     H       H      CH.sub.3                                                                            CH.sub.3                                                                            CH(CH.sub.3)CH═CH.sub.2                5-8     H       H      CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.2 C.tbd.CH                          5-9     H       H      CH.sub.3                                                                            CH.sub.3                                                                            CH(CH.sub.3)C.tbd.CH                       5-10    F       H      CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                   5-11    F       H      CH.sub.3                                                                            CH.sub.3                                                                            C.sub.2 H.sub.5                            5-12    F       H      CH.sub.3                                                                            CH.sub.3                                                                            .sup.i C.sub.3 H.sub.7                     5-13    F       H      CH.sub.3                                                                            CH.sub.3                                                                            .sup.n C.sub.3 H.sub.7                     5-14    F       H      CH.sub.3                                                                            CH.sub.3                                                                            .sup.i C.sub.4 H.sub.9                     5-15    F       H      CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.2 CH═CH.sub.2                   5-16    F       H      CH.sub.3                                                                            CH.sub.3                                                                            CH(CH.sub.3)CH═CH.sub.2                5-17    F       H      CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.2 C.tbd.CH                          5-18    F       H      CH.sub.3                                                                            CH.sub.3                                                                            CH(CH.sub.3)C.tbd.CH                       5-19    H       H      CF.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                   5-20    H       H      CF.sub.3                                                                            CH.sub.3                                                                            C.sub.2 H.sub.5                            5-21    H       H      CF.sub.3                                                                            CH.sub.3                                                                            .sup.i C.sub.3 H.sub.7                     5-22    H       H      CF.sub.3                                                                            CH.sub.3                                                                            .sup.n C.sub.3 H.sub.7                     5-23    H       H      CF.sub.3                                                                            CH.sub.3                                                                            .sup.i C.sub.4 H.sub.9                     5-24    H       H      CF.sub.3                                                                            CH.sub.3                                                                            CH.sub.2 CH═CH.sub.2                   5-25    H       H      CF.sub.3                                                                            CH.sub.3                                                                            CH(CH.sub.3)CH═CH.sub.2                5-26    H       H      CF.sub.3                                                                            CH.sub.3                                                                            CH.sub.2 C.tbd.CH                          5-27    H       H      CF.sub.3                                                                            CH.sub.3                                                                            CH(CH.sub.3)C.tbd.CH                       5-28    F       H      CF.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                   5-29    F       H      CF.sub.3                                                                            CH.sub.3                                                                            C.sub.2 H.sub.5                            5-30    F       H      CF.sub.3                                                                            CH.sub.3                                                                            .sup.i C.sub.3 H.sub.7                     5-31    F       H      CF.sub.3                                                                            CH.sub.3                                                                            .sup.i C.sub.4 H.sub.9                     5-32    F       H      CF.sub.3                                                                            CH.sub.3                                                                            CH.sub.2 CH═CH.sub.2                   5-33    F       H      CF.sub.3                                                                            CH.sub.3                                                                            CH(CH.sub.3)CH═CH.sub.2                5-34    F       H      CF.sub.3                                                                            CH.sub.3                                                                            CH.sub.2 C.tbd.CH                          5-35    F       H      CF.sub.3                                                                            CH.sub.3                                                                            CH(CH.sub.3)C.tbd.CH                       ______________________________________                                    

The following will describe production examples for compound [2] whichis an intermediate compound for the production of the present compounds.

Intermediate Production Example 1

First, 7.5 g of ethyl E- and Z-2-(4'-chlorophenyl)-3-methoxyacrylate wasdissolved in 180 ml of ethanol, to which 11.0 g of acetamnidinehydrochloride and 16.1 g of potassium carbonate were added, and themixture was stirred at 60° C. for 2.5 hours. The reaction mixture wascooled to room temperature, neutralized by the addition of acetic acid,and concentrated. The precipitated crystals were collected byfiltration, washed with water, and dried, which afforded 6.5 g ofcompound 1- 1002.

¹ H--NMR (60 MHz, DMSO-d₆): δ (ppm) 2.30 (3 H, s), 7.35 (2 H, d, J=9Hz), 7.70 (2 H, d, J=9 Hz), 8.05 (1 H, s)

Intermediate Production Example 2

First, 2.8 g of ethyl E- andZ-2-(2',4'-difluorophenyl)-3-methoxyacrylate was dissolved in 70 ml ofethanol, to which 4.1 g of acetamidine hydrochloride and 6.0 g ofpotassium carbonate were added, and the mixture was stirred at 60° C.for 3 hours. The reaction mixture was cooled to room temperature,neutralized by the addition of acetic acid, and concentrated. Theprecipitated crystals were collected by filtration, washed with water,and dried, which afforded 2.0 g of compound 1-1004.

Intermediate Production Example 3

First, 1.5 ml of trifluoroacetamidine was added to 1.0 g of ethyl2-(4'-chlorophenyl)-2-formylacetate, and the mixture was stirred at roomtemperature for 5 hours. After completion of the reaction, the reactionmixture was subjected to silica gel chromatography, which afforded 0.3 gof compound 1-1008.

¹ H--NMR (60 MHz, CDCl₃ +DMSO-d₆): δ (ppm) 7.30 (2 H, d, J=9 Hz), 7.55(2 H, d, J=9 Hz), 8.30. (H, s)

Intermediate Production Example 4

First, 1.0 ml of trifluoroacetamidine was added to 1.0 g of ethyl E- andZ-2-(4'-chlorophenyl)-3-methoxyacrylate, followed by stirring for 3hours, to which 0.5 ml of trifluoroacetamidine was further added, andthe mixture was stirred at 60° C. for 4 hours. The reaction mixture wascooled to room temperature and subjected to silica gel chromatography,which afforded 0.8 g of compound 1-1008. The physical properties are thesame as those obtained in Intermediate Production Example 3.

Intermnediate Production Example 5

First, 5.0 ml of trifluoroacetamidine was added to 5.0 g of ethyl2-(2',4'-difluorophenyl)-2-formylacetate, and the mixture was stirred atroom temperature for 17 hours. After completion of the reaction, thereaction mixture was subjected to silica gel chromatography, whichafforded 0.5 g of compound 1-1010.

¹ H--NMR (250 MHz, CDCl₃ +DMSO-d₆): δ (ppm) 6.80-7.00 (2 H, m),7.45-7.55 (1 H, m), 7.94 (1 H, s)

Intermediate Production Example 6

First, 7 ml of trifluoroacetamidine was added to 6.9 g of ethyl E- andZ-2-(2',4'-difluorophenyl)-3-methoxyacrylate, and the mixture wasstirred at room temperature for 23 hours. After completion of thereaction, the reaction mixture was subjected to silica gelchromatography, which afforded 3.9 g of compound 1-1010. The physicalproperties are the same as those obtained in Intermediate ProductionExample 5.

Intermediate Production Exanple 7

First, 5.15 g of ethyl E- andZ-2-(2',4'-dichlorophenyl)-3-methoxyacrylate was dissolved in 150 ml ofethanol, to which 6.08 g of acetamidine hydrochloride and 11.02 g ofpotassium carbonate were added, and the mixture was stirred at 60° C.for 3.5 hours. After completion of the reaction, the reaction mixturewas cooled to room temperature, neutralized by the addition of aceticacid, and concentrated. The precipitated crystals were collected byfiltration and dried, which afforded 4.35 g of compound 1-1013, m.p.250° C. or higher (decomp.).

Intermediate Production Example 8

First, 10 ml of trifluoroacetamidine was added to 2.2 g of ethyl (E- andZ-) 2-(4'-chloro-2'-fluoro-5'-isopropoxy)-3-methoxyacrylate, and themixture was stirred at room temperature for 28 hours. After completionof the reaction, the reaction mixture was subjected to silica gel columnchromatography, which afforded 2.0 g of compound 1-1014.

¹ H--NMR (250 MHz, CDCl₃): δ (ppm) 1.34 (6 H, d, J=6.0 Hz), 4.44 (1 H,hp, J=6 Hz), 6.82 (1 H, d, J=6.6 Hz), 7.00 (1 H, d, J=7.8 Hz), 8.18 (1H, s)

Intermediate Production Example 9

First, 5 ml of trifluoroacetamidine was added to 4.0 g of ethyl E- andZ-2-(4'-fluorophenyl)-3-methoxyacrylate, and the reaction was allowed toproceed at room temperature for 47 hours. After completion of thereaction, the reaction mixture was subjected to silica gel columnchromatography, which afforded 3.5 g of compound 1-1007.

¹ H--NMR (250 MHz, CDCl₃): δ (ppm) 7.05 (2 H, dd, J=9.7, 9.7 Hz), 7.62(2 H, dd, J=5.5, 9.7 Hz), 8.23 (1 H, s)

Intermediate Production Example 10

First, 5.0 ml of trifluoroacetamidine was added to 3.0 g of ethyl E- andZ-2-(2',4'-dichlorophenyl)-3-methoxyacrylate, and the reaction wasallowed to proceed for 5 days. After completion of the reaction, thereaction mixture was subjected to. silica gel column chromatography,which afforded 3.5 g of compound 1-1015 as a crude product.

Intermediate Production Example 11

First, 50 g of trifluoroacetamidine was added to 34 g of ethyl E- andZ-2-(4'-chloro-2'-fluorophenyl)-3-methoxyacrylate, and the reaction wasallowed to proceed for 4 days. After completion of the reaction, thereaction mixture was subjected to silica gel column chromatography,which afforded 25.6 g of compound 1-1011.

¹ H--NMR (250 MHz, CDCl₃): δ (ppm) 7.05-7.12 (2 H, m), 7.40 (1 H, dd,J=7.9, 7.9 Hz), 8.21 (1 H, d, J=1.2 Hz)

Examples of compound [2] are shown with their compound numbers in Tables6 to 8.

                  TABLE 6                                                         ______________________________________                                        Compound of the formula:                                                       ##STR44##                                                                    Compound                                                                      No.       X       Y       R.sup.1                                                                            R.sup.2                                                                             B                                        ______________________________________                                        1-1001    H       F       H    CH.sub.3                                                                            H                                        1-1002    H       Cl      H    CH.sub.3                                                                            H                                        1-1003    H       Br      H    CH.sub.3                                                                            H                                        1-1004    F       F       H    CH.sub.3                                                                            H                                        1-1005    F       Cl      H    CH.sub.3                                                                            H                                        1-1006    F       Br      H    CH.sub.3                                                                            H                                        1-1007    H       F       H    CF.sub.3                                                                            H                                        1-1008    H       Cl      H    CF.sub.3                                                                            H                                        1-1009    H       Br      H    CF.sub.3                                                                            H                                        1-1010    F       F       H    CF.sub.3                                                                            H                                        1-1011    F       Cl      H    CF.sub.3                                                                            H                                        1-1012    F       Br      H    CF.sub.3                                                                            H                                        1-1013    Cl      Cl      H    CH.sub.3                                                                            H                                        1-1014    F       Cl      H    CF.sub.3                                                                            OCH(CH.sub.3).sub.2                      1-1015    Cl      Cl      H    CF.sub.3                                                                            H                                        ______________________________________                                    

                  TABLE 7                                                         ______________________________________                                        Compound of the formula:                                                       ##STR45##                                                                    Compound                                                                      No.       X       Y      Z.sup.2                                                                             R.sup.1                                                                            R.sup.2                                                                              R.sup.6                            ______________________________________                                        3-1001    H       F      O     H    CH.sub.3                                                                             CH.sub.3                           3-1002    H       Cl     O     H    CH.sub.3                                                                             CH.sub.3                           3-1003    H       Br     O     H    CH.sub.3                                                                             CH.sub.3                           3-1004    F       F      O     H    CH.sub.3                                                                             CH.sub.3                           3-1005    F       Cl     O     H    CH.sub.3                                                                             CH.sub.3                           3-1006    F       Br     O     H    CH.sub.3                                                                             CH.sub.3                           3-1007    H       F      O     H    CH.sub.3                                                                             C.sub.2 H.sub.5                    3-1008    H       Cl     O     H    CH.sub.3                                                                             C.sub.2 H.sub.5                    3-1009    H       Br     O     H    CH.sub.3                                                                             C.sub.2 H.sub.5                    3-1010    F       F      O     H    CH.sub.3                                                                             C.sub.2 H.sub.5                    3-1011    F       Cl     O     H    CH.sub.3                                                                             C.sub.2 H.sub.5                    3-1012    F       Br     O     H    CH.sub.3                                                                             C.sub.2 H.sub.5                    3-1013    H       F      O     H    CF.sub.3                                                                             CH.sub.3                           3-1014    H       Cl     O     H    CF.sub.3                                                                             CH.sub.3                           3-1015    H       Br     O     H    CF.sub.3                                                                             CH.sub.3                           3-1016    F       F      O     H    CF.sub.3                                                                             CH.sub.3                           3-1017    F       Cl     O     H    CF.sub.3                                                                             CH.sub.3                           3-1018    F       Br     O     H    CF.sub.3                                                                             CH.sub.3                           3-1019    H       F      O     H    CF.sub.3                                                                             C.sub.2 H.sub.5                    3-1020    H       Cl     O     H    CF.sub.3                                                                             C.sub.2 H.sub.5                    3-1021    H       Br     O     H    CF.sub.3                                                                             C.sub.2 H.sub.5                    3-1022    F       F      O     H    CF.sub.3                                                                             C.sub.2 H.sub.5                    3-1023    F       Cl     O     H    CF.sub.3                                                                             C.sub.2 H.sub.5                    3-1024    F       Br     O     H    CF.sub.3                                                                             C.sub.2 H.sub.5                    ______________________________________                                    

                  TABLE 8                                                         ______________________________________                                        Compound of the formula:                                                       ##STR46##                                                                    Compound                                                                      No.       X      Y      R.sup.1                                                                            R.sup.2                                                                             R.sup.7                                                                             R.sup.8                              ______________________________________                                        4-1001    H      F      H    CH.sub.3                                                                            H     CH.sub.3                             4-1002    H      Cl     H    CH.sub.3                                                                            H     CH.sub.3                             4-1003    H      Br     H    CH.sub.3                                                                            H     CH.sub.3                             4-1004    H      F      H    CH.sub.3                                                                            H     CH.sub.2 OH                          4-1005    H      Cl     H    CH.sub.3                                                                            H     CH.sub.2 OH                          4-1006    H      Br     H    CH.sub.3                                                                            H     CH.sub.2 OH                          4-1007    H      F      H    CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                             4-1008    H      Cl     H    CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                             4-1009    H      Br     H    CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                             4-1010    H      F      H    CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.2 OH                          4-1011    H      Cl     H    CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.2 OH                          4-1012    H      Br     H    CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.2 OH                          4-1013    F      F      H    CH.sub.3                                                                            H     CH.sub.3                             4-1014    F      Cl     H    CH.sub.3                                                                            H     CH.sub.3                             4-1015    F      Br     H    CH.sub.3                                                                            H     CH.sub.3                             4-1016    F      F      H    CH.sub.3                                                                            H     CH.sub.2 OH                          4-1017    F      Cl     H    CH.sub.3                                                                            H     CH.sub.2 OH                          4-1018    F      Br     H    CH.sub.3                                                                            H     CH.sub.2 OH                          4-1019    F      F      H    CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                             4-1020    F      Cl     H    CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                             4-1921    F      Br     H    CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                             4-1022    F      F      H    CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.2 OH                          4-1023    F      Cl     H    CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.2 OH                          4-1024    F      Br     H    CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.2 OH                          4-1025    H      F      H    CF.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                             4-1026    H      Cl     H    CF.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                             4-1027    H      Br     H    CF.sub.3                                                                            H     CH.sub.3                             4-1028    H      F      H    CF.sub.3                                                                            H     CH.sub.2 OH                          4-1029    H      Cl     H    CF.sub.3                                                                            H     CH.sub.2 OH                          4-1030    H      Br     H    CF.sub.3                                                                            H     CH.sub.2 OH                          4-1031    H      F      H    CF.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                             4-1032    H      Cl     H    CF.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                             4-1033    H      Br     H    CF.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                             4-1034    H      F      H    CF.sub.3                                                                            CH.sub.3                                                                            CH.sub.2 OH                          4-1035    H      Cl     H    CF.sub.3                                                                            CH.sub.3                                                                            CH.sub.2 OH                          4-1036    H      Br     H    CF.sub.3                                                                            CH.sub.3                                                                            CH.sub.2 OH                          4-1037    F      F      H    CF.sub.3                                                                            H     CH.sub.3                             4-1038    F      Cl     H    CF.sub.3                                                                            H     CH.sub.3                             4-1039    F      Br     H    CF.sub.3                                                                            H     CH.sub.3                             4-1040    F      F      H    CF.sub.3                                                                            H     CH.sub.2 OH                          4-1041    F      Cl     H    CF.sub.3                                                                            H     CH.sub.2 OH                          4-1042    F      Br     H    CF.sub.3                                                                            H     CH.sub.2 OH                          4-1043    F      F      H    CF.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                             4-1044    F      Cl     H    CF.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                             4-1045    F      Br     H    CF.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                             4-1046    F      F      H    CF.sub.3                                                                            CH.sub.3                                                                            CH.sub.2 OH                          4-1047    F      Cl     H    CF.sub.3                                                                            CH.sub.3                                                                            CH.sub.2 OH                          4-1048    F      Br     H    CF.sub.3                                                                            CH.sub.3                                                                            CH.sub.2 OH                          ______________________________________                                    

The following will describe production examples for compounds [5] and[27] which are starting compounds for the production of the presentcompounds.

Reference Example 1

Production of ethyl 2-(4'-chlorophenyl)-2-formylacetate and ethyl E- andZ-2-(4'-chlorophenyl)-3-methoxyacrylate

First, 17.24 g of 4-chlorophenylacetic acid was dissolved in 200 ml ofethanol, to which a catalytic amount of p-toluenesulfonic acid wasadded, and the mixture was heated under reflux for 10 hours. Aftercompletion of the reaction, the reaction mixture was cooled to roomtemperature and concentrated. The residue was poured into water andextracted with ethyl acetate, and the organic layer was dried and thenconcentrated. The residue was subjected to silica gel chromatography,which afforded 19.0 g of ethyl 4-chlorophenylacetate.

Then, 4.19 g of sodium hydride (60% in oil) was suspended in 150 ml oftetrahydrofuran, to which a solution of 19.0 g of ethyl4-chlorophenylacetate in 150 ml of tetrahydrofuran was added dropwise at5° to 10° C. After stirring at room temperature for 1.5 hours, 8.42 g ofethyl formate was added, and the mixture was further stirred at roomtemperature for 4.5 hours. After completion of the reaction, thereaction mixture was cooled to ice temperature, neutralized by theaddition of diluted hydrochloric acid, and concentrated. The residue wassubjected to phase separation with ethyl acetate-water, and the organiclayer was dried and then concentrated. The residue was subjected tosilica gel chromatography, which afforded 17.0 g of ethyl2-(4'-chlorophenyl)-2-formylacetate.

Then, 1.93 g of sodium hydride (60% in oil) was suspended in 90 ml of1,2-dimethoxyethane, to which 90 ml of a solution of ethyl2-(4'-chlorophenyl)-2-formylacetate was added dropwise at 5° to 10° C.After stirring at room temperature for 1.1/3 hours, 11.76 g of methyliodide was added dropwise, and the mixture was further stirred at roomtemperature for 20 hours. After completion of the reaction, the reactionmixture was cooled with ice, and excess sodium hydride was decomposed bythe addition of water, followed by extraction with ethyl acetate-water.The organic layer was dried and then concentrated, and the residue wassubjected to silica gel chromatography, which afforded 7.58 g of ethylE- and Z-2-(4'-chlorophenyl)-3-methoxyacrylate.

Reference Example 2

Production of ethyl 2-(2',4'-difluorophenyl)-2-formylacetate and ethylE- and Z-2-(2',4'-difluorophenyl)-3-methoxyacrylate

Ethyl 2-(2',4'-difluorophenyl)-2-formylacetate and ethyl E- andZ-2-(2',4'-difluorophenyl)-3-methoxyacrylate were synthesized with2,4-difluorophenylacetate as the starting compound in the same manner asdescribed in Reference Example 1.

Reference Example 3

Production of ethyl 2-(2',4'-dichlorophenyl)-2-formylacetate and ethylE- and Z-2-(2',4'-dichlorophenyl)-3-methoxyacrylate

Ethyl 2-(2',4'-dichlorophenyl)-2-formylacetate and ethyl E- andZ-2-(2',4'-dichlorophenyl)-3-methoxyacrylate were synthesized with2,4-dichlorophenylacetate as the starting compound in the same manner asdescribed in Reference Example 1.

Reference Example 4

Production of ethyl2-(4-chloro-2-fluoro-5-isopropoxyphenyl)-2-formylacetate and ethyl (E-and Z-) 2-(4'-chloro-2'-fluoro-5'-isopropoxy)-3-methoxyacrylate

(1) First, 250 ml of water and 25 ml of concentrated sulfuric acid wereadded to 30 g of 4-chloro-2-fluoro-5-isopropoxyaniline, and the mixturewas stirred at 50° C. for 2.5 hours and then cooled to 0° C., to which asolution of 10.4 g of sodium nitrite in 80 ml of water was slowly addeddropwise. The solution of a diazonium salt thus formed was addeddropwise to a solution of 150 g of potassium iodide in 300 ml of waterat room temperature, and the mixture was stirred for at room temperaturefor 45 minutes. After completion of the reaction, the reaction mixturewas extracted with diethyl ether, and the organic layer was washed withsaturated sodium chloride solution, dried, and concentrated. The residuewas subjected to silica gel column chromatography, which afforded 36 gof 2-chloro-4-fluoro-5-iodo-1-isopropoxybenzene.

¹ H--NMR (250 MHz, CDCl₃): δ (ppm) 1.36 (6 H, d, J=6.2 Hz), 4.46 (1 H,hp, J=6.2 Hz), 7.11 (1 H, d, J=7.2 Hz), 7.27 (1 H, d, J=5.7 Hz)

(2) Then, 62.9 g of 2-chloro-4-fluoro-5-iodo-1-isopropoxybenzene, 20.4 gof sodium formate, and 2.81 g ofdichlorobis(triphenylphosphine)palladium were dissolved in 120 ml ofN,N-dimethylformamide, which was stirred at 90° to 100° C. for 12 hours,while bubbling carbon monoxide thereinto. After completion of thereaction, the reaction mixture was cooled to room temperature, to whichdiluted hydrochloric acid was added, and the mixture was extracted withethyl acetate. The organic layer was washed with saturated sodiumchloride solution, dried, and concentrated. The residue was subjected tosilica gel column chromatography, which afforded 15 g of4-chloro-2-fluoro-5-isopropoxybenzaldehyde.

¹ H--NMR (300 MHz, CDCl₃): δ (ppm) 1.31 (6 H, d, J=6.3 Hz), 4.52 (1 H,hp, J=6.3 Hz), 7.18 (1 H, d, J=9.7 Hz), 7.29 (1 H, d, J=6.1 Hz), 10.2 (1H, s)

(3) Then, 7.5 g of 4-chloro-2-fluoro-5-isopropoxybenzaldehyde wasdissolved in 70 ml of 1,4-dioxane and 5 ml of methanol, to which 0.92 gof sodium borohydride was added at 5° C., and the mixture was stirredfor 40 minutes. After completion of the reaction, a small amount ofdiluted hydrochloric acid was added, and the reaction mixture was pouredinto water and extracted with ethyl acetate. The organic layer waswashed with saturated sodium chloride solution, dried, and concentrated.The residue was subjected to silica gel column chromatography, whichafforded 6.7 g of 4-chloro-2-fluoro-5-isopropoxybenzyl alcohol.

¹ H--NMR (250 MHz, CDCl₃): δ (ppm) 1.36 (6 H, d, J=6.0 Hz), 1.96 (1 H,br), 4.49 (1 H, hp, J=6.0 Hz), 4.71 (1 H, d, J=5.2 Hz), 7.04 (1 H, d,J=6.7 Hz), 7.09 (1 H, d, J=9.2 Hz)

(4) Then, 6.7 g of 4-chloro-2-fluoro-5-isopropoxybenzylalcohol wasdissolved in 70 ml of tetrahydrofuran, to which 1 ml of pyridine wasadded, and the mixture was cooled to 5° C.. Then, 5 ml of thionylchloride was slowly added dropwise at 5° to 10° C., and the mixture wasstirred at 5° C. for 1.5 hours. After completion of the reaction, thereaction mixture was filtered to separate the precipitated crystals, andthe filtrate was concentrated. The residue was subjected to silica gelcolumn chromatography, which afforded 7.3 g of4-chloro-2-fluoro-5-isopropoxybenzyl chloride.

¹ H--NMR (300 MHz, CDCl₃): δ (ppm) 1.37 (6 H, d, J=6.0 Hz), 4.49 (1 H,hp, J=6.0 Hz), 4.57 (2 H, s), 6.99 (1 H, d, J=6.8 Hz), 7.13 (1 H, d,J=9.2 Hz)

(5) Then, 7.3 g of 4-chloro-2-fluoro-5-isopropoxybenzyl chloride wasdissolved in 70 ml of ethanol and 30 ml of water, to which 1.8 g ofsodium cyanide was added, and the mixture was heated under reflux for 2hours. After completion of the reaction, the reaction mixture was pouredinto water and extracted with ethyl acetate. The organic layer waswashed with saturated sodium chloride solution, dried, and concentrated.The residue was subjected to silica gel column chromatography, which 7.0g of 4-chloro-2-fluoro-5-isopropoxyphenylacetonitrile.

¹ H--NMR (250 MHz, CDCl₃): δ (ppm) 1.38 (6 H, d, J=5.9 Hz), 3.73 (2 H,s), 4.51 (1 H, hp, J=5.9 Hz), 7.00 (1 H, d, J=6.8 Hz), 7.16 (1 H, d,J=9.0 Hz)

(6) Then, 7.0 g of 4-chloro-2-fluoro-5-isopropoxyphenylacetonitrile wasdissolved in 100 ml of ethanol, to which 5 ml of sulfuric acid, and themixture was heated under reflux for 66 hours. After completion of thereaction, the reaction mixture was poured into water and extracted withethyl acetate. The organic layer was washed with saturated sodiumchloride solution, dried, and concentrated. The residue was subjected tosilica gel column chromatography, which afforded 7.2 g of ethyl4-chloro-2-fluoro-5-isopropoxyphenyl acetate.

¹ H--NMR (250 MHz, CDCl₃): δ (ppm) 1.26 (3 H, t, J=7.1 Hz), 1.36 (6 H,d, J=6.0 Hz), 3.60 (2 H, s), 4.17 (2 H, q, J=7.1 Hz), 4.46 (1 H, hp,J=6.0 Hz), 6.87 (1 H, d, J=6.8 Hz), 7.10 (1 H, d, J=9.0 Hz)

(7) Then, 1.1 g of sodium hydride (60% in oil) was suspended in 50 ml oftetrahydrofuran, and the mixture was cooled to 5° C., to which asolution of 7.2 g of ethyl 4-chloro-2-fluoro-5-isopropoxyphenylacetatein 80 ml of tetrahydrofuran was slowly added dropwise. The mixture wasstirred for 30 minutes with a gradual temperature increase to roomtemperature, to which 10 ml of ethyl formate was added at roomtemperature, followed by stirring for 3 hours. Then, the reactionmixture was cooled to 5° C., to which diluted hydrochloric acid wasadded. The reaction mixture was concentrated, and the residue was pouredinto water and extracted with ethyl acetate. The organic layer waswashed with saturated sodium chloride solution, dried, and concentrated.The residue was subjected to silica gel column chromatography, whichafforded 8.0 g of ethyl2-(4-chloro-2-fluoro-5-isopropoxyphenyl)-2-formylacetate.

¹ H--NMR (300 MHz, CDCl₃): δ (ppm) 1.26 (3 H, t, J=7.0 Hz), 1.36 (6 H,d, J=6.2 Hz), 4.26 (2 H, q, J=7.0 Hz), 4.45 (1 H, hp, J=6.2 Hz), 6.76(1/2 H, s), 6.78 (1/2 H, s), 7.10 (1 H, d, J=8.9 Hz), 7.26 (1 H, d,J=12.6 Hz), 12.1 (1/2 H, s), 12.2 (1/2 H, s)

(8) Then, 1.1 g of sodium hydride (60% in oil) was suspended in 50 ml of1,2-dimethoxyethane, and the mixture was cooled to 5° C., to which asolution of 8.0 g of ethyl2-(4-chloro-2-fluoro-5-isopropoxyphenyl)-2-formylacetate in 50 ml of1,2-dimethoxyethane was slowly added dropwise. The mixture was stirredfor 20 minutes with a gradual temperature increase to room temperature,to which 3.0 ml of methyl iodide was added at room temperature, followedby stirring for 4.5 hours. Then, the reaction mixture was cooled to 5°C., to which diluted aqueous hydrochloric acid was added. The reactionmixture was poured into water and extracted with ethyl acetate. Theorganic layer was washed with saturated sodium chloride solution, dried,and concentrated. The residue was subjected to silica gel columnchromatography, which afforded 5.5 g of ethyl (E- andZ-)2-(4'-chloro-2'-fluoro-5'-isopropoxyphenyl)-3-methoxyacrylate.

Reference Example 5

Production of ethyl E- and Z-2-(4'-fluorophenyl)-3-methoxyacrylate

Ethyl E- and Z-2-(4'-fluorophenyl)-3-methoxyacrylate was synthesizedwith 4-fluorophenylacetate as the starting compound in the same manneras described in

Reference Example 1. Reference Example 6

Production of ethyl E- andZ-2-(4'-chloro-2'-fluorophenyl)-3-methoxyacrylate

(1) First, 25 g of 4-chloro-2-fluorobenzaldehyde was dissolved in amixed solvent consisting of 250 ml of 1,4-dioxane and 25 ml of methanol,to which 2.4 g of sodium borohydride was added under ice cooling, andthe mixture was stirred for 30 minutes. After completion of thereaction, a small amount of diluted aqueous hydrochloric acid was added,and the reaction mixture was poured into water and extracted with ethylacetate. The organic layer was washed with saturated sodium chloridesolution, dried, and concentrated. The residue was subjected to silicagel column chromatography, which afforded 25 g of4-chloro-2-fluorobenzyl alcohol.

¹ H--NMR (300 MHz, CDCl₃): δ (ppm) 1.82 (1 H, t, J=6.1 Hz), 4.72 (2 H,d, J=6.1 Hz), 7.08 (1 H, dd, J=2.1, 9.8 Hz), 7.15 (1 H, dd, J=2.1, 8.2Hz), 7.37 (1 H, dd, J=8.2, 8.2 Hz)

(2) Then, 16.5 g of 4-chloro-2-fluorobenzylalcohol was dissolved in 150ml of tetrahydrofuran and 1 ml of pyridine, to which 10 ml of thionylchloride was added dropwise at 5° C., and the mixture was stirred for2.5/6 hours. After cormpletion of the reaction, the reaction mixture wasconcentrated, and the precipitated crystals were collected byfiltration. The filtrate was subjected to silica gel columnchromatography, which afforded 18.5 g of 4-chloro-2-fluorobenzylchloride.

¹ H--NMR (250 MHz, CDCl₃): δ (ppm) 4.59 (2 H, s), 7.09-7.17 (2 H, m),7.36 (1 H, dd, J=7.9, 7.9 Hz)

(3) Then, 18.5 g of 4-chloro-2-fluorobenzyl chloride was dissolved in amixed solvent consisting of 130 ml of ethanol and 30 ml of water, towhich 5.3 g of sodium cyanide was added, and the mixture was heatedunder reflux for 2 hours. After completion of the reaction, the reactionmixture was allowed to stand for cooling to room temperature, pouredinto water, and extracted with ethyl acetate. The organic layer waswashed with saturated sodium chloride solution, dried, and concentrated.The residue was subjected to silica gel column chromatography, whichafforded 15.1 g of 4-chloro-2-fluorophenylacetonitrile.

¹ H--NMR (250 MHz, CDCl₃): δ (ppm) 3.74 (2 H, s), 7.12-7.22 (2 H, m),7.39 (1 H, dd, J=8.0, 8.0 Hz)

(4) Then, 15.1 g of 4-chloro-2-fluorophenylacetonitrile was dissolved in150 ml of ethanol, to which 10 ml of suiliric acid was added, and themixture was heated under reflux for 65 hours. After completion of thereaction, the reaction mixture was poured into water and extracted withethyl acetate. The organic layer was washed with saturated sodiumchloride solution, dried, and concentrated. The residue was subjected tosilica gel column chromatography, which afforded 17.8 g of ethyl4-chloro-2-fluorophenylacetate.

¹ H--NMR (250 MHz, CDCl₃): δ (ppm) 1.25 (3 H, t, J=7.1 Hz), 3.63 (2 H,s), 4.17 (2 H, q, J=7.1 Hz), 7.07-7.24 (3 H, m)

(5) Then, 3.6 g of sodium hydride (60% in oil) was suspended in 120 mlof tetrahydrofuran, and the mixture was cooled to 5° C., to which asolution of 17.8 g of ethyl 4-choro-2-fluorophenylacetate in 120 ml oftetrahydrofuran was slowly added drop-wise. The mixture was stirred for30 minutes with a gradual temperature increase to room temperature, towhich 20 ml of ethyl formate was added at room temperature, followed bystirring for 3 hours. Then, the reaction mixture was cooled with ice, towhich diluted aqueous hydrochloric acid was added. The reaction mixturewas poured into water and extracted with ethyl acetate. The organiclayer was washed with saturated sodium chloride solution, dried, andconcentrated. The residue was subjected to silica gel columnchromatography, which afforded 19.1 g of ethyl2-(4-chloro-2-fluorophenyl)-2-formylacetate.

¹ H--NMR (250 MHz, CDCl₃): δ (ppm) 1.25 (1/2×3 H, t, J=7.1 Hz), 1.26(1/2×3 H, t, J=7.1 Hz), 4.26 (2 H, q, J=7.1 Hz), 7.07-7.26 (3 H, m),9.74 (1/2 H, br), 9.80 (1/2 H, br)

(6) Then, 3.4 g of sodium hydride (60% in oil) was suspended in 120 mlof 1,2-dimethoxyethane, and the mixture was cooled to 5° C., to which asolution of 19.1 g of ethyl 2-(4-chloro-2-fluorophenyl)-2-formylacetatein 120 ml of 1,2-dimethoxyethane was slowly added dropwise. The mixturewas stirred for 30 minutes with a gradual temperature increase to roomtemperature, to which 10 ml of methyl iodide at room temperature, andthe mixture was stirred for 3.1/3 hours. Then, the reaction mixture wascooled with ice, to which diluted aqueous hydrochloric acid was added.The reaction mixture was poured into water and extracted with ethylacetate. The organic layer was washed with saturated sodium chloridesolution, dried, and concentrated, The residue was subjected to silicagel column chromatography, which afforded 11.1 g of ethyl E- andZ-2-(4'-chloro-2'-fluorophenyl)-3-methoxyacrylate.

The following will describe formulation examples for the presentcompounds, where the present compounds are designated by their compoundnumbers shown in Tables 1 to 5 and parts are by weight.

Formulation Example 1

Fifty parts of each of compounds 1-1 to 1-715, 2-1 to 2-380, 3-1 to3-256, 4-1 to 4-272, and 5-1 to 5-35, 3 parts of calciumligninsulfonate, 2 parts of sodium laurylsulfate, and 45 parts ofsynthetic hydrated silicon oxide are well pulverized and mixed to give awettable powder for each compound.

Formulation Example 2

Ten parts of each of compounds 1-1 to 1-715, 2-1 to 2-380, 3-1 to 3-256,4-1 to 4-272, and 5-1 to 5-35, 14 parts of polyoxyethylene styryl phenylether, 6 parts of calcium dodecylbenzenesulfonate, 35 parts of xylene,and 35 parts of cyclohexanone are well mixed to give an emulsifiableconcentrate for each compound.

Formulation Example 3

Two parts of each of compounds 1-1 to 1-715, 2-1 to 2-380, 3-1 to 3-256,4-1 to 4-272, and 5-1 to 5-35, 2 parts of synthetic hydrated siliconoxide, 2 parts of calcium ligninsulfonate, 30 parts of bentonite, and 64parts of kaoline clay are well pulverized and mixed, to which water isadded, and the mixture is well kneaded, granulated, and dried to give agranule for each compound.

Formulation Example 4

Twenty-five parts of each of compounds 1-1 to 1-715, 2-1 to 2-380, 3-1to 3-256, 4-1 to 4-272, and 5-1 to 5-35, 50 parts of 10% aqueouspolyvinyl alcohol solution, and 25 parts of water are mixed, and themixture is pulverized until the average particle size becomes 5 μm orless to give a flowable for each compound.

The following test examples will demonstrate that the present compoundsare useful as active ingredients of herbicides. The present compoundsare designated by their compound numbers shown in Tables 1 to 5.

The herbicidal activity was evaluated at 6 levels with indices of 0 to5, i.e., designated by the numeral "0", "1", "2", "3", "4" or "5",wherein "0" means that there was no or little difference in the degreeof germination or growth between the treated and the untreated testplants at the time of examination, and "5" means that the test plantsdied complete or their germination or growth was completely inhibited.The herbicidal activity is excellent when rated at "4" or "5" butinsufficient when rated at "3" or lower.

Test Example 1

Foliar treatment on upland fields

Cylindrical plastic pots of 10 cm in diameter and 10 cm in depth werefilled with soil, in which the seeds of velvetleaf (Abutilontheophrasti) were sowed, and the test plants were grown in a greenhousefor 15 days. Each of the test compounds listed below was formulated intoan emulsifiable concentrate according to Formulation Example 2, whichwas diluted with water containing a spreading agent to a prescribedconcentration. The dilution was uniformly sprayed over the foliage ofthe test plants with a sprayer at a volume of 1000 liters per hectare.After the application, the test plants were grown in the greenhouse for15 days, and the herbicidal activity was examined. The results are shownin Table 9.

                  TABLE 9                                                         ______________________________________                                                  Application amount of                                               Test      active ingredient                                                                           Herbicidal activity                                   compound  (g/ha)        Velvetleaf                                            ______________________________________                                        1-5       2000          4                                                     1-10      2000          4                                                     1-335     2000          5                                                     1-340     2000          5                                                     1-662     2000          4                                                     2-203     125           5                                                     2-251     125           5                                                     2-252     125           5                                                     ______________________________________                                    

Test Example 2

Soil surface treatment on upland fields

Cylindrical plastic pots of 10 cm in diameter and 10 cm in depth werefilled with soil, in which the seeds of velvetleaf (Abutilontheophrasti) were sowed. Each of the test compounds listed below wasformulated into an emulsifiable concentrate according to FormulationExample 2, which was diluted with water to a prescribed concentration.The dilution was uniformly sprayed over the soil surface in the potswith a sprayer at a volume of 1000 liters per hectare. After theapplication, the test plants were grown in a greenhouse for 19 days, andthe herbicidal activity was examined. The results are shown in Table 10.

                  TABLE 10                                                        ______________________________________                                                  Application amount of                                               Test      active ingredient                                                                           Herbicidal activity                                   compound  (g/ha)        Velvetleaf                                            ______________________________________                                        1-335     2000          5                                                     1-668     500           5                                                     2-251     500           5                                                     ______________________________________                                    

Test Example 3

Flooding treatment on paddy fields

Cylindrical plastic pots of 9 cm in diameter and 11 cm in depth werefilled with soil, in which the seeds of barnyardgrass (Echinochloaoryzicola) were sowed. These pots were flooded to form a paddy field,and the test plants were grown in a greenhouse for 7 days. Each of thetest compounds listed below was formulated into an emulsifiableconcentrate according to Formulation Example 2, which was diluted withwater to a prescribed concentration. The dilution was applied to thewater surface in the pots with a syringe at a volume of 50 liters perare. After the application, the test plants were grown in the greenhousefor 19 days, and the herbicidal activity was examined.. The results areshown in Table 11.

                  TABLE 11                                                        ______________________________________                                                  Application amount of                                               Test      active ingredient                                                                           Herbicidal activity                                   compound  (g/ha)        Barnyardgrass                                         ______________________________________                                        1-335     1000          5                                                     1-340     1000          5                                                     2-251     250           5                                                     ______________________________________                                    

Test Example 4

Foliar treatment on upland fields

Cylindrical plastic pots of 10 cm in diameter and 10 cm in depth werefilled with soil, in which the seeds of velvetleaf (Abutilontheophrasti) and barnyardgrass (Echinochloa crus-galli) were sowed, andthe test plants were grown in a greenhouse for 15 days. Each of the testcompounds listed below was formulated into an emulsifiable concentrateaccording to Formulation Example 2, which was diluted with watercontaining a spreading agent to a prescribed concentration. The dilutionwas uniformly sprayed over the foliage of the test plants with a sprayerat a volume of 1000 liters per hectare. After the application, the testplants were grown in the greenhouse for 15 days, and the herbicidalactivity was examined. The results are shown in Table 12.

                  TABLE 12                                                        ______________________________________                                                Application amount of                                                 Test    active ingredient                                                                            Herbicidal activity                                    compound                                                                              (g/ha)         Barnyardgrass                                                                             Velvetleaf                                 ______________________________________                                        1-341   500            5           5                                          1-367   500            5           5                                          1-391   500            4           5                                          1-420   500            5           5                                          1-482   500            4           5                                          1-486   500            5           5                                          1-487   500            4           5                                          1-491   500            5           5                                          1-495   500            5           5                                          1-496   500            4           5                                          1-499   500            5           5                                          1-503   500            5           5                                          1-504   500            5           5                                          1-663   500            5           5                                          1-667   500            5           5                                          1-668   500            5           5                                          2-252   500            5           5                                          ______________________________________                                    

Test Example 5

Soil surface treatment on upland fields

Cylindrical plastic pots of 10 cm in diameter and 10 cm in depth werefilled with soil, in which the seeds of velvetleaf (Abutilontheophrasti) and barnyardgrass (Echinochloa crus-galli) were sowed. Eachof the test compounds listed below was formulated into an emulsifiableconcentrate according to Formulation Example 2, which was diluted withwater to a prescribed concentration. The dilution was uniformly sprayedover the soil surface in the pots with a sprayer at a volume of 1000liters per hectare. After the application, the test plants were grown inthe greenhouse for 19 days, and the herbicidal activity was examined.The results are shown in Table 13.

                  TABLE 13                                                        ______________________________________                                                Application amount of                                                 Test    active ingredient                                                                            Herbicidal activity                                    compound                                                                              (g/ha)         Barnyardgrass                                                                             Velvetleaf                                 ______________________________________                                        1-341   2000           5           5                                          1-367   2000           5           5                                          1-391   2000           4           5                                          1-420   2000           5           5                                          1-482   2000           5           5                                          1-486   2000           5           5                                          1-487   2000           5           5                                          1-491   2000           5           5                                          1-495   2000           5           5                                          1-496   2000           5           5                                          1-499   2000           4           5                                          1-503   2000           5           5                                          1-504   2000           5           5                                          1-663   2000           5           5                                          1-667   2000           5           5                                          2-203   2000           5           5                                          2-251   2000           5           5                                          2-252   2000           5           5                                          ______________________________________                                    

Test Example 6

Flooding treatment on paddy fields

Cylindrical plastic pots of 9 cm in diameter and 11 cm in depth werefilled with soil, in which the seeds of barnyardgrass (Echinochloaoryzicola) and hardstem bulrush (Scirpus juncoides) were sowed. Thesepots were flooded to form a paddy field, and the test plants were grownin a greenhouse for 7 days. Each of the test compounds listed below wasformulated into an emulsifiable concentrate according to FormulationExample 2, which was diluted with water to a prescribed concentration.The dilution was applied to the water surface in the pots with a syringeat a volume of 50 liters per are. After the application, the test plantswere grown in the greenhouse for 19 days, and the herbicidal activitywas examined. The results are shown in Table 14.

                  TABLE 14                                                        ______________________________________                                                Application amount of                                                                        Herbicidal activity                                    Test    active ingredient          Hardstem                                   compound                                                                              (g/ha)         Barnyardgrass                                                                             bulrush                                    ______________________________________                                        1-341   250            5           5                                          1-347   250            5           4                                          1-367   250            5           5                                          1-420   250            5           5                                          1-482   250            5           5                                          1-486   250            5           5                                          1-487   250            5           5                                          1-491   250            5           5                                          1-495   250            5           5                                          1-496   250            5           5                                          1-499   250            5           4                                          1-503   250            5           4                                          1-504   250            5           5                                          1-663   250            5           5                                          1-667   250            5           5                                          1-668   250            5           5                                          2-203   250            5           5                                          2-251   250            5           4                                          2-252   250            5           5                                          ______________________________________                                    

Test Example 7

Foliar treatment on upland fields

Plastic pots of 26.5×19 cm² in area and 7 cm in depth were filled withsoil, in which the seeds of ivyleaf morningglory (Ipomoea hederacea),common cocklebur (Xanthium pensylvanicum), common ragweed (Ambrosiaartemisiifolia), and barnyardgrass (Echinochloa crus-galli) were sowedand grown so that the application of a chemical to these weed specieswas made after 23, 27, 30, and 17 days from sowing, respectively. Eachof the test compounds listed below was formulated into an emulsifiableconcentrate according to Formulation Example 2, which, was diluted withwater to a prescribed concentration. The dilution was uniformly sprayedover the foliage of the test plants with a sprayer at a volume of 1050liters per hectare. At this time, the unfavorable weeds, although theirgrowth stage was different depending upon the weed species, were at the2- to 4-leaf stage, and the plant height was 8 to 18 cm. After 21 daysfrom the application, the herbicidal activity was examined. The resultsare shown in Table 15. This test was made in a greenhouse over the testperiod.

                  TABLE 15                                                        ______________________________________                                        Application                                                                   amount of    Herbicidal activity                                                     active             Ivyleaf                                             Test   ingredient                                                                              Common   morning-                                                                             Common Barnyard-                             compound                                                                             (g/ha)    cocklebur                                                                              glory  ragweed                                                                              grass                                 ______________________________________                                        1-367  250       5        5      5      4                                     1-420  250       5        5      5      5                                     1-486  250       5        5      5      5                                     1-491  250       5        5      5      4                                     1-495  250       5        5      5      5                                     1-496  250       5        5      5      4                                     1-499  250       5        5      5      5                                     1-503  250       5        5      5      5                                     1-504  250       5        5      5      5                                     1-667  250       5        5      5      5                                     2-203  250       5        5      4      5                                     2-252  250       5        5      5      5                                     ______________________________________                                    

What is claimed is:
 1. A compound of the formula: ##STR47## wherein R¹ is hydrogen or C₁ -C₃ alkyl; R² is C₁ -C₃ alkyl substituted with one or more halogen atoms; R³ is C₁ -C₆ alkyl optionally substituted with one or more halogen atoms, C₃ -C₆ alkenyl, or C₃ -C₆ alkynyl; and Q is [Q-1], [Q-2], [Q-3], [Q-4], or [Q-5] of the formula: ##STR48## wherein X is hydrogen or halogen; Y is halogen, nitro, cyano, or trifluoromethyl;Z¹ is oxygen, sulfur, NH, or methylene; Z² is oxygen or sulfur; n is 0 or 1; B is hydrogen, halogen, nitro, cyano, chlorosulfonyl, --OR¹⁰, --SR¹⁰, --SO₂ --OR¹⁰, --N(R¹⁰)R¹¹, --SO₂ N(R¹¹)R¹², --NR¹¹ (COR¹³), --NR¹¹ (SO₂ R¹⁴), --N(SO₂ R¹⁴) --(SO₂ R¹⁵), --N(SO₂ R¹⁴)(COR¹³), --NHCOOR¹³, --COOR¹³, --CON(R¹¹)R¹², --CSN(R¹¹)R¹², --COR¹⁶, --CR¹⁷ ═CR¹⁸ CHO, --CR¹⁷ ═CR¹⁸ COOR¹³, CR¹⁷ ═CR¹⁸ CON(R¹¹)R¹², --CH₂ CHWCOOR¹³ or --CH₂ CHWCON(R¹¹)R¹², wherein W is hydrogen, chlorine or bromine; R¹⁰ is hydrogen, C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₃ -C₈ cycloalkyl, C₃ -C₆ alkenyl, C₃ -C₆ haloalkenyl, C₃ -C₆ alkynyl, C₃ -C₆ haloalkynyl, cyano C₁ -C₆ alkyl, C₂ -C₈ alkoxyalkyl, C₂ -C₈ alkylthioalkyl, carboxy C₁ -C₆ alkyl, (C₁ -C₆ alkoxy)carbonyl C₁ -C₆ alkyl, (C₁ -C₆ haloalkoxy)carbonyl C₁ -C₆ alkyl, {(C₁ -C₄ alkoxy) C₁ -C₄ alkoxy}carbonyl C₁ -C₆ alkyl, (C₃ -C₈ cycloalkoxy)carbonyl C₁ -C6 alkyl, --CH₂ CON(R¹¹)R¹², --CH₂ COON(R¹¹)R¹², --CH(C₁ -C₄ alkyl)CON(R¹¹)R¹², or --CH(C₁ -C₄ alkyl)COON(R¹¹)R¹² ; R¹¹ and R¹² are independently hydrogen, C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₃ -C₆ alkenyl, C₃ -C₆ alkynyl, cyano C₁ -C₆ alkyl, C₂ -C₈ alkoxyalkyl, C₂ -C₈ alkylthioalkyl, carboxy C₁ -C₆ alkyl, (C₁ -C₆ alkoxy)carbonyl C₁ -C₆ alkyl, or {(C₁ -C₄ alkoxy) C₁ -C₄ alkoxy}carbonyl C₁ -C₆ alkyl, or R¹¹ and R¹² are taken together to form tetramethylene, pentamethylene, or ethyleneoxyethylene; R¹³ is hydrogen, C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, or C₃ -C₈ cycloalkyl; R¹⁴ and R¹⁵ are independently C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, or phenyl optionally substituted with methyl or nitro; R¹⁶ is hydrogen, C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₂ -C₆ alkenyl, C₂ -C₆ haloalkenyl, C₂ -C₆ alkynyl, C₂ -C₆ haloalkynyl, C₂ -C₈ alkoxyalkyl, or hydroxy C₁ -C₆ alkyl; and R¹⁷ and R¹⁸ are independendly hydrogen or C₁ -C₆ alkyl; R⁴ is hydrogen or C₁ -C₃ alkyl; R⁵ is hydrogen, C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₃ -C₆ alkenyl, C₃ -C₆ haloalkenyl, C₃ -C₆ alkynyl, C₃ -C₆ haloalkynyl, cyano C₁ -C₆ alkyl, C₂ -C₈ alkoxyalkyl, C₃ -C₈ alkoxyalkoxyalkyl, carboxy C₁ -C₆ alkyl, (C₁ -C₆ alkoxy)carbonyl C₁ -C₆ alkyl, {(C₁ -C₄ alkoxy)C₁ -C₄ alkoxy}carbonyl C₁ -C₆ alkyl, (C₃ -C₈ cycloalkoxy)carbonyl-C₁ -C₆ alkyl, --CH₂ CON(R¹¹)R¹², --CH₂ COON(R¹¹)R¹², --CH(C₁ -C₄ alkyl)CON(R¹¹)R¹², --CH(C₁ -C₄ alkyl)COON(R¹¹)R¹², C₂ -C₈ alkylthioalkyl, C₁ -C₆ alkylsulfonyl, C₁ -C₆ haloalkylsulfonyl, (C₁ -C₈ alkyl)carbonyl, (C₁ -C₈ alkoxy)carbonyl, or hydroxy C₁ -C₆ alkyl; R⁶ is C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, formyl, cyano, carboxyl, hydroxy C₁ -C₆ alkyl, C₁ -C₆ alkoxy C₁ -C₆ alkyl, C₁ -C₆ alkoxy C₁ -C₆ alkoxy C₁ -C₆ alkyl, (C₁ -C₆ alkyl)carbonyloxy C₁ -C₆ alkyl, (C₁ -C₆ haloalkyl)carbonyloxy C₁ -C₆ alkyl, (C₁ -C₆ alkoxy)carbonyl, or (C₁ -C₆ alkyl)carbonyl; R⁷ is hydrogen or C₁ -C₆ alkyl; and R⁸ is C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₁ -C₆ hydroxyalkyl, C₂ -C₈ alkoxyalkyl, C₃ -C₁₀ alkoxyalkoxyalkyl, (C₁ -C₅ alkyl)carbonyloxy C₁ -C₆ alkyl, (C₁ -C₆ haloalkyl)carbonyloxy C₁ -C₆ alkyl, carboxyl, carboxy C₁ -C₆ alkyl, (C₁ -C₈ alkoxy)carbonyl, (C₁ -C₆ haloalkoxy)carbonyl, (C₃ -C₁₀ cycloalkoxy)carbonyl, (C₃ -C₈ alkenyloxy)carbonyl, (C₃ -C₈ alkynyloxy)carbonyl, aminocarbonyl, (C₁ -C₆ alkyl)aminocarbonyl, di(C₁ -C₆ alkyl)aminocarbonyl, (C₁ -C₆ alkyl)aminocarbonyloxy C₁ -C₆ alkyl, or di(C₁ -C₆ alkyl)aminocarbonyloxy C₁ -C₆ alkyl.
 2. A compound according to claim 1, wherein Q is [Q-1], [Q-2], [Q-3], or [Q4];Y is halogen; Z¹ is oxygen or sulfur; Z² is oxygen; B is hydrogen, nitro, --OR¹⁰, --SR¹⁰, --NHR¹⁰, --NHSO₂ R¹⁴, --COOR¹³, or --CH₂ CHWCOOR¹³, wherein W is hydrogen or chlorine; R¹⁰ is C₁ -C₆ alkyl, C₃ -C₈ cycloalkyl, C₃ -C₆ alkenyl, C₃ -C₆ haloalkenyl, C₃ -C₆ alkynyl, cyano C₁ -C₆ alkyl, or (C₁ -C₆ alkoxy)carbonyl C₁ -C₆ alkyl; R¹³ is C₁ -C₆ alkyl; and R¹⁴ is C₁ -C₆ alkyl; R⁵ is C₁ -C₆ alkyl, C₃ -C₆ alkenyl, or C₃ -C₆ alkynyl; R⁶ is C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, formyl, hydroxymethyl, C₁ -C₆ alkoxymethyl, C₁ -C₆ alkylcarbonyloxymethyl, or C₁ -C₆ alkoxycarbonyl; R⁷ is hydrogen or methyl; and R⁸ is methyl, hydroxymethyl, C₁ -C₆ alkoxymethyl, (C₁ -C₅ alkyl)carbonyloxymethyl, carboxyl, or (C₁ -C₆ alkoxy)carbonyl.
 3. A compound according to claim 1 or 2, wherein R² is trifluoromethyl.
 4. A compound according to claim 1, wherein Q is [Q-1].
 5. A compound according to claim 1, wherein Q is [Q-2].
 6. A compound according to claim 1, wherein Q is [Q-3].
 7. A compound according to claim 1, wherein Q is [Q4].
 8. A compound according to claim 2, wherein Q is [Q-1].
 9. A compound according to claim 2, wherein Q is [Q-2].
 10. A compound according to claim 2, wherein Q is [Q-3].
 11. A compound according to claim 2, wherein Q is [Q4].
 12. A compound according to claim 2, wherein Q is [Q-1; and R² is trifluoromethyl.
 13. A compound according to claim 2, wherein Q is [Q-2]; and R² is trifluoromethyl.
 14. A compound according to claim 2, wherein Q is [Q-3]; and R² is trifluoromethyl.
 15. A compound according to claim 2, wherein Q is [Q-4]; and R² is trifluoromethyl.
 16. A compound according to claim 2, wherein Q is [Q-1]; R² is trifluoromethyl; and B is --OR¹⁰.
 17. A compound according to claim 2, wherein Q is [Q-1]; R² is trifluoromethyl; and B is --NHR¹⁰.
 18. A compound according to claim 2, wherein Q is [Q-1]; R² is trifluoromethyl; B is --OR¹⁰ ; and R¹⁰ is C₃ -C₆ alkynyl.
 19. A compound according to claim 2, wherein Q is [Q-1]; R² is trifluoromethyl; B is --OR¹⁰ ; and R¹⁰ is (C₁ -C₆ aLkoxy)carbonyl C₁ -C₆ alkyl.
 20. A compound according to claim 2, wherein Q is [Q-1]; R² is trifluoromethyl; B is --OR¹⁰ ; and R¹⁰ is 1-(C₁ -C₆ alkoxy)carbonylethyl.
 21. A compound according to claim 2, wherein Q is [Q-1]; R² is trifluoromethyl; B is --OR¹⁰ ; and R¹⁰ is (C₁ -C₆ alkoxy)carbonylmethyl.
 22. A compound according to claim 2, wherein Q is [Q-2]; R² is trifluoromethyl; Z¹ is oxygen; n is 1; R⁴ is hydrogen; and R⁵ is C₃ -C₆ alkynyl.
 23. A compound according to claim 1, wherein R¹ is hydrogen; R² is trifluoromethyl; R³ is methyl; Q is [Q-1]; X is fluorine; Y is chlorine; and B is propargyloxy.
 24. A compound according to claim 1, wherein R¹ is hydrogen; R² is trifluoromethyl; R³ is methyl; Q is [Q-1]; X is fluorine; Y is chlorine; and B is 1-(ethoxycarbonyl)ethoxy.
 25. A compound according to claim 1, wherein R¹ is hydrogen; R² is trifluoromethyl; R³ is methyl; Q is [Q-1]; X is fluorine; Y is chlorine; and B is 1-(methoxycarbonyl)ethoxy.
 26. A compound according to claim 1, wherein R¹ is hydrogen; R² is trifluoromethyl; R³ is methyl; Q is [Q-2]; X is fluorine; Z¹ is oxygen; n is 1; R⁴ is hydrogen; and R⁵ is propargyl.
 27. A process for producing a compound according to claim 1, which comprises reacting a compound of the formula: ##STR49## wherein R¹ is hydrogen or C₁ -C₃ alkyl; R² is C₁ -C₃ alkyl substituted with one or more halogen atoms; and Q is [Q-1], [Q-2], [Q-3], [Q4] or [Q-5] as defined in claim 1, with a compound of the formula:

    R.sup.3 --D                                                [3]

wherein R³ is C₁ -C₆ alkyl optionally substituted with one or more halogen atoms, C₃ -C₆ alkenyl, or C₃ -C₆ alkynyl; and D is chlorine, bromine, iodine, methanesulfonyloxy, trifluoromethanesulfonyloxy, or p-toluenesulfonyloxy.
 28. A herbicidal composition comprising, as an active ingredient, a herbicidally effective amount of the compound according to claim 1, and an inert carrier or diluent.
 29. A method for controlling unfavorable weeds, which comprises applying a herbicidally effective amount of the compound according to claim 1 to an area where the unfavorable weeds grow or will grow.
 30. A compound of the formula: ##STR50## wherein R¹ is hydrogen or C₁ -C₃ alkyl; R²¹ is trifluoromethyl; and Q' is [Q'-1], [Q-2], [Q'-3], [Q'-4], or [Q-5] of the formula: ##STR51## wherein X is hydrogen or halogen; Y' is halogen;Z¹ is oxygen, sulfur, NH, or methylene; Z² is oxygen or sulfur; n is 0or 1; B is hydrogen, halogen, nitro, cyano, chlorosulfonyl, --OR¹⁰, --SR¹⁰, --SO_(2--OR) ¹⁰, --N(R¹⁰)R¹¹, --SO₂ N(R¹¹)R¹², --NR¹¹ (COR¹³), --NR¹¹ (SO₂ R¹⁴), --N(SO₂ R¹⁴)--(SO₂ R¹⁵), --N(SO₂ R¹⁴)(COR¹³), --NHCOOR¹³, --COOR¹³, --CON(R¹¹)R¹², --CSN--(R¹¹)R¹², --COR¹⁶, --CR¹⁷ ═CR¹⁸ CHO, --CR¹⁷ ═CR¹⁸ COOR¹³, CR¹⁷ ═CR¹⁸ CON--(R¹¹)R¹², --CH₂ CHWCOOR¹³, or --CH₂ CHWCON(R¹¹)R¹², wherein W is hydrogen, chlorine or bromine; R¹⁰ is hydrogen, C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₃ -C₈ cycloalkyl, C₃ -C₆ alkenyl, C₃ -C₆ haloalkenyl, C₃ -C₆ alkynyl, C₃ -C₆ haloalkynyl, cyano C₁ -C₆ alkyl, C₂ -C₈ alkoxyalkyl, C₂ -C₈ alkylthioalkyl, carboxy C₁ -C₆ alkyl, (C₁ -C₆ alkoxy)carbonyl C₁ -C₆ alkyl, (C₁ -C₆ haloalkoxy)carbonyl C₁ -C₆ alkyl, {(C₁ -C₄ alkoxy) C₁ -C₄ alkoxy}carbonyl C₁ -C₆ alkyl, (C₃ -C₈ cycloalkoxy)carbonyl C₁ -C₆ alkyl, --CH₂ CON(R¹¹)R¹², --CH₂ COON(R¹¹)R¹², --CH(C₁ -C₄ alkyl)CON(R¹¹)R¹², or --CH(C₁ -C₄ alkyl)COON(R¹¹)R¹² ; R¹¹ and R¹² are independently hydrogen, C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₃ -C₆ alkenyl, C₃ -C₆ alkynyl cyano C₁ -C₆ alkyl, C₂ -C₈ alkoxyalkyl, C₂ -C₈ alkylthioalkyl, carboxy C₁ -C₆ alkyl, (C₁ -C₆ alkoxy)carbonyl C₁ -C₆ alkyl, or {(C₁ -C₄ alkoxy) C₁ -C₄ alkoxy}carbonyl C₁ -C₆ alkyl, or R¹¹ and R¹² are taken together to form tetramethylene, pentamethylene, or ethyleneoxyethylene; R¹³ is hydrogen, C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, or C₃ -C₈ cycloalkyl; R¹⁴ and R¹⁵ are independently C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, or phenyl optionally substituted with methyl or nitro; R¹⁶ is hydrogen, C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₂ -C₆ alkenyl, C₂ -C₆ haloalkenyl, C₂ -C₆ alkynyl, C₂ -C₆ haloalkynyl, C₂ -C₈ alkoxyalkyl, or hydroxy C₁ -C₆ alkyl; and R¹⁷ and R¹⁸ are independently hydrogen or C₁ -C₆ alkyl; R⁴ is hydrogen or C₁ -C₃ alkyl, R⁵ is hydrogen, C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₃ -C₆ alkenyl, C₃ -C₆ haloalkenyl, C₃ -C₆ alkynyl, C₃ -C₆ haloalkynyl, cyano C₁ -C₆ alkyl, C₂ -C₈ alkoxyalkyl, C₃ -C₈ alkoxyalkoxyalkyl, carboxy C₁ -C₆ alkyl, (C₁ -C₆ alkoxy)carbonyl C₁ -C₆ alkyl, {(C₁ -C₄ alkoxy) C₁ -C₄ alkoxylcarbonyl C₁ -C₆ alkyl, (C₃ -C₈ cycloalkoxy)carbonyl-C₁ -C₆ alkyl, --CH₂ CON(R¹¹)R¹², --CH₂ COON(R¹¹)R¹², --CH(C₁ -C₄ alkyl)CON(R¹¹)R¹², --CH(C₁ -C₄ alkyl)COON(R¹¹)R¹², C₂ -C₈ alkylthioalkyl, C₁ -C₆ alkylsulfonyl, C₁ -C₆ haloalkylsulfonyl, (C₁ -C₈ alkyl)carbonyl, (C₁ -C₈ alkoxy)carbonyl, or hydroxy C₁ -C₆ alkyl; R⁶ is C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, formyl, cyano, carboxyl, hydroxy C₁ -C₆ alkyl, C₁ -C₆ alkoxy C₁ -C₆ alkyl, C₁ -C₆ alkoxy C₁ -C₆ alkoxy C₁ -C₆ alkyl, (C₁ -C₆ alkyl)carbonyloxy C₁ -C₆ alkyl, (C₁ -C6 haloalkyl)carbonyloxy C₁ -C₆ alkyl, (C₁ -C₆ alkoxy)carbonyl, or (C₁ -C₆ alkyl)carbonyl; R⁷ is hydrogen or C₁ -C₆ alkyl; and R⁸ is C₁ -C₆ alkyl, C₁ -C₆ haloalkyl, C₁ -C₆ hydroxyalkyl, C2-C₈ alkoxyalkyl, C₃ -C₁₀ alkoxyalkoxyalkyl, (C₁ -C₅ alkyl)carbonyloxy C₁ -C₆ alkyl, (C₁ -C₆ haloalkyl)carbonyloxy C₁ -C₆ alkyl, carboxyl, carboxy C₁ -C₆ alkyl, (C₁ -C₈ alkoxy)carbonyl, (C₁ -C₆ haloalkoxy)carbonyl, (C₃ -C₁₀ cycloalkoxy)carbonyl, (C₃ -C₈ alkenyloxy)carbonyl, (C₃ -C₈ alkynyloxy)carbonyl, aminocarbonyl, (C₁ -C₆ alkyl)aminocarbonyl, di(C₁ -C₆ alkyl)aminocarbonyl, (C₁ -C₆ alkyl)aminocarbonyloxy C₁ -C₆ alkyl, or di(C₁ -C₆ alkyl)aminocarbonyloxy C₁ -C₆ alkyl.
 31. A compound according to claim 30, wherein Q is [Q'-1].
 32. A process for producing a compound of the formula: ##STR52## wherein Q' is [Q'-1], [Q-2], [Q'-3], [Q'-4] or [Q-5] as defined in claim 31; R¹ is hydrogen or C₁ -C₃ alkyl; and R²¹ is trifluoromethyl, which comprises reacting a compound of the formula: ##STR53## wherein Q' and R¹ are as defined above; and R¹⁹ and R²⁰ are independently C₁ -C₃ alkyl, with a compound of the formula: ##STR54## wherein R²¹ is as defined above. 